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The ship 's primary armament consisted of four 30 @.@ 5 cm ( 12 in ) 45 @-@ caliber guns in two twin gun turrets . This was augmented by a heavy secondary battery of eight 24 cm ( 9 @.@ 4 in ) guns in four wing turrets . The tertiary battery consisted of twenty 10 cm L / 50 guns in casemated single mounts , four 47 mm ( 1 @.@ 85 in ) L / 44 and one 47 mm L / 33 quick @-@ firing guns . Furthermore , the ship 's boats were equipped with two 66 mm ( 2 @.@ 6 in ) landing guns for operations shore . Three 45 cm ( 17 @.@ 7 in ) torpedo tubes were also carried , one on each broadside and one in the stern .
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= = Service history = =
|
[
796,
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4809,
2106,
796,
796,
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] |
The ship was assigned to the Austro @-@ Hungarian Fleet 's 1st Battle Squadron after her 1911 commissioning . In 1912 , Zrínyi and her two sister ships conducted two training cruises into the eastern Mediterranean Sea . On the second cruise into the Aegean Sea , conducted from November to December , Zrínyi and her sister ships were accompanied by the cruiser SMS Admiral Spaun and a pair of destroyers . After returning to Pola , the entire fleet mobilized for possible hostilities , as tensions flared in the Balkans .
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In 1913 , Zrínyi participated in an international naval demonstration in the Ionian Sea to protest the Balkan Wars . Ships from other navies included in the demonstration were the British pre @-@ dreadnought HMS King Edward VII , the Italian pre @-@ dreadnought Ammiraglio di Saint Bon , the French armored cruiser Edgar Quinet , and the German light cruiser SMS Breslau . The most important action of the combined flotilla , which was under the command of British Admiral Cecil Burney , was to blockade the Montenegrin coast . The goal of the blockade was to prevent Serbian reinforcements from supporting the siege at Scutari , where Montenegro had besieged a combined force of Albanians and Ottomans . Pressured by the international blockade , Serbia withdrew its army from Scutari , which was subsequently occupied by a joint Allied ground force .
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During that year , the first of four new dreadnoughts , SMS Viribus Unitis , that made up the Tegetthoff class — the only dreadnoughts built for the Austro @-@ Hungarian Navy — came into active service . With the commissioning of these dreadnoughts , Zrínyi and her sisters were moved from the 1st Division to the 2nd Division of the 1st Battle Squadron .
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= = = World War I = = =
|
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At that time of the assassination of Archduke Franz Ferdinand of Austria on 28 June 1914 , the battleships in the Austro @-@ Hungarian Navy consisted of the Radetzky class , the Tegetthoff class ( which still had one ship , SMS Szent István , under construction ) , the Erzherzog Karl class and finally , the older Habsburg class . Along with the remainder of the Austro @-@ Hungarian Navy , Zrínyi was mobilized in late July 1914 to support the flight of SMS Goeben and SMS Breslau . The two German ships broke out of Messina , which was surrounded by the British navy and reached Turkey . The flotilla had advanced as far south as Brindisi in southeastern Italy when news of the successful breakout reached Vienna . The Austro @-@ Hungarian ships were then recalled before seeing action .
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On 23 May 1915 , between two and four hours after news of the Italian declaration of war reached the main Austro @-@ Hungarian naval base at Pola , Zrínyi and the rest of the fleet departed to bombard the Italian and Montenegrin coast . Their focus was on the important naval base at Ancona , and later the coast of Montenegro . The bombardment of Montenegro was part of the larger Austro @-@ Hungarian campaign against the Kingdoms of Montenegro and Serbia , who were members of the Entente , during the first half of 1915 . The attack on Ancona was an immense success , and the ships were unopposed during the operation . The bombardment of the province and the surrounding area resulted in the destruction of an Italian steamer in the port of Ancona itself , and an Italian destroyer , Turbine , was severely damaged further south . On the shore , the infrastructure of the port of Ancona , as well as the surrounding towns , were severely damaged . The railroad yard in Ancona , as well as the port facilities in the town , were damaged or destroyed . The local shore batteries were also suppressed . During the bombardment , Zrínyi also helped to destroy a train , a railway station , and a bridge at Senigallia . Additional targets that were damaged or destroyed included wharves , warehouses , oil tanks , radio stations , and the local barracks . Sixty @-@ three Italians , both civilians and military personnel , were killed in the bombardment . By the time Italian ships from Taranto and Brindisi arrived on the scene , the Austro @-@ Hungarians were safely back in Pola .
|
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The objective of the bombardment of Ancona was to delay the Italian Army from deploying its forces along the border with Austria @-@ Hungary by destroying critical transportation systems . The surprise attack on Ancona succeeded in delaying the Italian deployment to the Alps for two weeks . This delay gave Austria @-@ Hungary valuable time to strengthen its Italian border and re @-@ deploy some of its troops from the Eastern and Balkan fronts .
|
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Aside from the attack on Ancona , the Austro @-@ Hungarian battleships were largely confined to Pola for the duration of the war . Their operations were limited by Admiral Anton Haus , the commander of the Austro @-@ Hungarian Navy , who believed that he would need to husband his ships to counter any Italian attempt to seize the Dalmatian coast . Since coal was diverted to the newer Tegetthoff @-@ class battleships , the remainder of the war saw Zrínyi and the rest of the Austro @-@ Hungarian Navy acting as a fleet in being . This resulted in the Allied blockade of the Otranto Strait . With his fleet blockaded in the Adriatic Sea , and with a shortage of coal , Haus followed a strategy based on mines and submarines designed to reduce the numerical superiority of the Allied navies .
|
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= = = Post @-@ war fate = = =
|
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198
] |
After the Austro @-@ Hungarian Empire collapsed in 1918 , the Austrians wanted to turn the fleet over to the newly created State of Slovenes , Croats and Serbs ( later to become a part of the Kingdom of Yugoslavia ) in order to prevent the Italians from claiming the ships as spoils of war . However , the victorious Allies refused to acknowledge the conversations between the Austrians and the south Slavs and , in due course , reallocated the ships . The ship had been boarded by a scratch Yugoslav crew on 10 November 1918 , one day before the Armistice , and had left Pola with her sister ship , Radetzky . They were soon spotted by heavy Italian ships , so the two battleships hoisted American flags and sailed south along the Adriatic coast to Castelli Bay near Spalato ( also known as Split ) . They appealed for American naval forces to meet them and accept their surrender , which a squadron of United States Navy ( USN ) submarine chasers in the area did . She had apparently been turned over to the fledgling south Slav state , as it was a Croat naval officer , Korvettenkapitän Marijan <unk> , who presented the ship as a prize of war to representatives of the United States Navy on the afternoon of 22 November 1919 at Spalato ( Split ) in Dalmatia . Simultaneously she was commissioned as USS Zrínyi and Lieutenant E.E. <unk> , USN , assumed command . The initial American complement consisted of four officers and 174 enlisted men — the latter entirely composed of United States Navy Reserve Force personnel . The ship remained at anchor at Spalato for nearly a year while the negotiations that would determine her ultimate fate dragged on . Only once did she apparently turn her engines over , and that occurred during a severe gale that struck Spalato on 9 February 1920 .
|
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] |
On the morning of 7 November 1920 , Zrínyi was decommissioned . USS Chattanooga took her in tow and , assisted by Brooks and Hovey , towed the battleship to Italy . Under the terms of the treaties of Versailles and St. Germain , Zrínyi was ultimately turned over to the Italian government at Venice . She was broken up for scrap later that year and into 1921 .
|
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] |
= Geopyxis carbonaria =
|
[
796,
2269,
11081,
87,
271,
6588,
10312,
796,
220,
198
] |
Geopyxis carbonaria is a species of fungus in the genus Geopyxis , family Pyronemataceae . First described to science in 1805 , and given its current name in 1889 , the species is commonly known as the charcoal loving elf @-@ cup , dwarf acorn cup , stalked bonfire cup , or pixie cup . The small , goblet @-@ shaped fruitbodies of the fungus are reddish @-@ brown with a whitish fringe and measure up to 2 cm ( 0 @.@ 8 in ) across . They have a short , tapered stalk . Fruitbodies are commonly found on soil where brush has recently been burned , sometimes in great numbers . The fungus is distributed throughout many temperate regions of the Northern Hemisphere . It is found in Europe , Turkey , and North America . Although it is primarily a saprotrophic species , feeding on the decomposing organic matter remaining after a fire , it also forms biotrophic associations with the roots of Norway spruce .
|
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] |
= = Taxonomy = =
|
[
796,
796,
9241,
30565,
796,
796,
220,
198
] |
The fungus was first described scientifically in 1805 by Johannes Baptista von Albertini and Lewis David de Schweinitz as Peziza carbonaria . Mordecai Cubitt Cooke illustrated the fruitbodies , spores , and asci in his 1879 work <unk> , seu Icones fungorum . Figures of fungi from all parts of the world . In 1889 , Pier Andrea Saccardo transferred the fungus to the genus Geopyxis , giving the species its current name . <unk> carbonaria , published by Heinrich Rehm in 1884 , is a synonym of G. carbonaria . Louis @-@ Joseph <unk> proposed the variety Geopyxis carbonaria var. sessilis in 1937 , referring to forms producing fruitbodies without a stalk , but the taxon is not considered to have independent taxonomic significance . In 1860 Miles Berkeley and Moses Ashley Curtis described the species Peziza <unk> from collections made in Japan as part of the North Pacific Exploring and Surveying Expedition ( 1853 – 1856 ) . This taxon was synonymized with G. carbonaria by Mien Rifai in 1968 , a taxonomic opinion corroborated by Donald Pfister about a decade later .
|
[
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416,
3759,
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546,
257,
5707,
1568,
764,
220,
198
] |
The specific epithet carbonaria derives from the Latin word for " charcoal " . Common names given to the fungus include " charcoal loving elf @-@ cup " , " dwarf acorn cup " , " pixie cup " , and the British Mycological Society approved " stalked bonfire cup " .
|
[
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] |
= = Description = =
|
[
796,
796,
12489,
796,
796,
220,
198
] |
The fruitbodies ( <unk> ) of Geopyxis <unk> are cup shaped , 1 – 2 cm wide , and have fringed whitish margins . The inner spore @-@ bearing surface of the cup , the hymenium , is brick red and smooth , while the exterior surface is a dull yellow , and may be either smooth or have blister @-@ like spots ( pustules ) . The stipe is small ( 1 – 1 @.@ 5 mm long and 1 – 2 mm wide ) , whitish in color , and expands abruptly into the cup . The brownish flesh of the fungus is thin and brittle . It does not have any distinctive taste , but has an unpleasant smell when crushed in water . The edibility of the fungus is not known , but the fruitbodies are insubstantial and unlikely to be harvested for eating .
|
[
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549,
41321,
290,
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284,
307,
34262,
329,
6600,
764,
220,
198
] |
= = = Microscopic characteristics = = =
|
[
796,
796,
796,
4527,
1416,
16603,
9695,
796,
796,
796,
220,
198
] |
In mass , the spores are whitish . The spores are elliptical , smooth , hyaline , devoid of oil droplets ( <unk> ) , and have dimensions of 13 – 18 by 7 – 9 µm . They are thin walled and germinate and grow rapidly in vitro in the absence of external stimuli . The asci are 190 – 225 by 9 – 10 µm . The paraphyses are slightly club @-@ shaped , unbranched , and have irregular orange @-@ brown granules , with tips up to 5 µm wide , and are not forked or lobed . The hypothecium , the layer of cells below the hymenium , is made of densely packed , small irregular cells .
|
[
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] |
= = = Similar species = = =
|
[
796,
796,
796,
11014,
4693,
796,
796,
796,
220,
198
] |
The closely related <unk> elf cup ( Geopyxis <unk> ) has a pale orange to yellowish fruitbody that is deeply cup shaped before flattening in maturity , and its crushed flesh often has an odor of sulfur . It may be distinguished microscopically by its paraphyses , which lack the orange @-@ brown granules characteristic of G. carbonaria . It also has larger spores , measuring 14 – 22 by 8 – 11 µm . Unlike G. carbonaria , it grows on substrates other than burned wood , including mosses , and needle duff . <unk> <unk> , which grows habitats similar to G. carbonaria , is distinguished microscopically by its spores that contain two oil droplets . Other genera with similar species with which G. carbonaria may be confused in the field include Aleuria , Caloscypha , <unk> , and <unk> .
|
[
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5028,
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1390,
42853,
274,
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29,
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3056,
3102,
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837,
1279,
2954,
29,
837,
290,
1279,
2954,
29,
764,
220,
198
] |
= = Habitat and distribution = =
|
[
796,
796,
41950,
265,
290,
6082,
796,
796,
220,
198
] |
Geopyxis carbonaria is widespread on burned soil or charcoal in the spring and throughout the growing season . It is one of the most common pioneer species found on burned ground . The charred litter on the forest floor increases the underlying soil pH as well as the availability of minerals . Fruitbodies are produced from 16 to 139 weeks after a forest fire in areas with coniferous trees . Most fruitbodies are produced in the first year after a burn . The fungus prefers fruiting in microhabitats with thin <unk> duff near standing burned tree trunks . Geopyxis carbonaria fruitbodies are often found in the same post @-@ fire stands as morels , although the former is usually more abundant . Because the pixie cup fruits earlier than morels , it may serve as an indicator of imminent morel fruiting . Other cup fungi often found fruiting in the same area as G. carbonaria include those from the genera Aleuria , Anthracobia , Peziza , and <unk> .
|
[
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31,
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3584,
262,
1966,
318,
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517,
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279,
39291,
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30665,
837,
2631,
89,
23638,
837,
290,
1279,
2954,
29,
764,
220,
198
] |
The fungus is found in Europe ( from where it was originally described ) , and is widespread throughout North America . The North American distribution extends north to Alaska . In 2010 , it was reported for the first time from Turkey .
|
[
383,
39526,
318,
1043,
287,
2031,
357,
422,
810,
340,
373,
6198,
3417,
1267,
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329,
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640,
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198
] |
= = Ecology = =
|
[
796,
796,
39978,
796,
796,
220,
198
] |
Although primarily a saprotrophic fungus involved in the post @-@ fire breakdown of duff and coniferous roots , Geopyxis carbonaria has been shown to be capable of forming ectomycorrhizae with Norway spruce ( Picea abies ) . It had been demonstrated earlier in laboratory experiments that the fungus has a biotrophic interaction with lodgepole pine ( Pinus contorta ) . The hyphae of G. carbonaria were able to infect the cortex of the tree seedling , but did not penetrate the <unk> . These traits suggest that the fungus is a moderate pathogen , with limited ability to cause reductions in seed germination . Additionally , the fungus produces the enzyme polyphenol oxidase , and can break down the complex organic polymer lignin — features characteristic of saprotrophic fungi . The formation of a rudimentary Hartig net , a characteristic of mycorrhizal fungi , indicated that G. carbonaria might be capable of forming mutualistic relationships under the right conditions . <unk> and colleagues suggest that its below @-@ ground association with spruce roots protects it from physical damage in the event of a fire , and the extensive fruitbody production after a fire may reflect " a successful fungal escape from a dying host where the fungus no longer can maintain its biotrophic association " .
|
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2569,
6958,
739,
262,
826,
3403,
764,
1279,
2954,
29,
290,
7810,
1950,
326,
663,
2174,
2488,
12,
31,
2323,
8112,
351,
599,
26524,
11135,
17289,
340,
422,
3518,
2465,
287,
262,
1785,
286,
257,
2046,
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290,
262,
7667,
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2618,
3227,
706,
257,
2046,
743,
4079,
366,
257,
4388,
1257,
13528,
6654,
422,
257,
9950,
2583,
810,
262,
39526,
645,
2392,
460,
5529,
663,
3182,
313,
18191,
8112,
366,
764,
220,
198
] |
Large fruitings of the fungus are often associated with damage to the host tree , such as that which occurs with burning . A field study conducted in Norway demonstrated that fruit bodies were more likely to be found in areas that were heavily burned , compared to locations with light to moderate burning where the trees remained viable , or in clearcut areas . Fruiting was much denser in spruce forests — with up to 700 – 1000 fruitbodies per square meter — than in pine forests , where fruitbodies were sporadic . Fruitbodies grew by the millions in the year following the Yellowstone fires of 1988 .
|
[
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286,
262,
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5242,
287,
262,
614,
1708,
262,
47257,
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286,
12122,
764,
220,
198
] |
= Gold dollar =
|
[
796,
3561,
8872,
796,
220,
198
] |
The gold dollar or gold one @-@ dollar piece was a coin struck as a regular issue by the United States Bureau of the Mint from 1849 to 1889 . The coin had three types over its lifetime , all designed by Mint Chief Engraver James B. Longacre . The Type 1 issue had the smallest diameter of any United States coin ever minted .
|
[
383,
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393,
3869,
530,
2488,
12,
31,
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1115,
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18197,
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286,
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1829,
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1683,
21043,
276,
764,
220,
198
] |
A gold dollar had been proposed several times in the 1830s and 1840s , but was not initially adopted . Congress was finally galvanized into action by the increased supply of bullion caused by the California gold rush , and in 1849 authorized a gold dollar . In its early years , silver coins were being hoarded or exported , and the gold dollar found a ready place in commerce . Silver again circulated after Congress in 1853 required that new coins of that metal be made lighter , and the gold dollar became a rarity in commerce even before federal coins vanished from circulation because of the economic disruption caused by the American Civil War .
|
[
317,
3869,
8872,
550,
587,
5150,
1811,
1661,
287,
262,
45440,
82,
290,
47784,
82,
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475,
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286,
262,
3034,
19911,
4073,
416,
262,
1605,
7511,
1810,
764,
220,
198
] |
Gold did not again circulate in most of the nation until 1879 ; once it did , the gold dollar did not regain its place . In its final years , it was struck in small numbers , causing speculation by hoarders . It was also in demand to be mounted in jewelry . The regular issue gold dollar was last struck in 1889 ; the following year , Congress ended the series .
|
[
3561,
750,
407,
757,
49306,
287,
749,
286,
262,
3277,
1566,
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3720,
2162,
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2162,
262,
1708,
614,
837,
3162,
4444,
262,
2168,
764,
220,
198
] |
= = Background = =
|
[
796,
796,
25353,
796,
796,
220,
198
] |
In proposing his plan for a mint and a coinage system , Secretary of the Treasury Alexander Hamilton in 1791 proposed that the one @-@ dollar denomination be struck both as a gold coin , and as one of silver , representative of the two metals which he proposed be made legal tender . Congress followed Hamilton 's recommendation only in part , authorizing a silver dollar , but no coin of that denomination in gold .
|
[
554,
24634,
465,
1410,
329,
257,
21043,
290,
257,
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496,
1080,
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4986,
286,
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13419,
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837,
475,
645,
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286,
326,
47491,
287,
3869,
764,
220,
198
] |
In 1831 , the first gold dollar was minted , at the private mint of Christopher Bechtler in North Carolina . Much of the gold then being produced in the United States came from the mountains of North Carolina and Georgia , and the dollars and other small gold coins issued by Bechtler circulated through that region , and were now and then seen further away . Additional one @-@ dollar pieces were struck by August Bechtler , Christopher 's son .
|
[
554,
1248,
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837,
262,
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416,
2932,
1355,
21474,
1754,
837,
12803,
705,
82,
3367,
764,
220,
198
] |
Soon after the <unk> began to strike their private issues , Secretary of the Treasury Levi Woodbury became an advocate of having the Mint of the United States ( " Mint " , when described as an institution ) strike the one @-@ dollar denomination in gold . He was opposed by the Mint Director , Robert M. Patterson . Woodbury persuaded President Andrew Jackson to have pattern coins struck . In response , Patterson had Mint Second Engraver Christian Gobrecht break off work on the new design for the silver one @-@ dollar coin and work on a pattern for the gold dollar . Gobrecht 's design featured a Liberty cap surrounded by rays on one side , and a palm branch arranged in a circle with the denomination , date , and name of the country on the other .
|
[
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3128,
837,
290,
1438,
286,
262,
1499,
319,
262,
584,
764,
220,
198
] |
Consideration was given to including the gold dollar as an authorized denomination in the revisionary legislation that became the Mint Act of 1837 . The Philadelphia newspaper Public Ledger , in December 1836 , supported a gold dollar , stating that " the dollar is the smallest gold coin that would be convenient , and as it would be eminently so , neither silver nor paper should be allowed to take its place . " Nevertheless , after Mint Director Patterson appeared before a congressional committee , the provision authorizing the gold dollar was deleted from the bill .
|
[
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341,
373,
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8287,
42765,
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3869,
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373,
13140,
422,
262,
2855,
764,
220,
198
] |
= = Inception = =
|
[
796,
796,
554,
4516,
796,
796,
220,
198
] |
In January 1844 , North Carolina Representative James Iver McKay , the chairman of the Committee on Ways and Means , solicited the views of Director Patterson on the gold dollar . Patterson had more of Gobrecht 's pattern dollar struck to show to committee members , again advising against a coin that if issued would be only about a half inch ( 13 mm ) in diameter . He told Treasury Secretary John C. Spencer that the only gold coins of that size in commerce , the Spanish and Colombian half @-@ escudos , were unpopular and had not been struck for more than twenty years . This seemed to satisfy the committee as nothing more was done for the time , and when a gold dollar was proposed again in 1846 , McKay 's committee recommended against it .
|
[
554,
3269,
1248,
2598,
837,
2258,
5913,
19920,
3700,
314,
332,
37946,
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8900,
286,
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4606,
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621,
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812,
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5150,
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1248,
3510,
837,
37946,
705,
82,
5583,
7151,
1028,
340,
764,
220,
198
] |
Even before 1848 , record amounts of gold were flowing to American mints to be struck into coin , but the California Gold Rush vastly increased these quantities . This renewed calls for a gold dollar , as well as for a higher denomination than the eagle ( $ 10 piece ) , then the largest gold coin . In January 1849 , McKay introduced a bill for a gold dollar , which was referred to his committee . There was much discussion in the press about the proposed coin ; one newspaper published a proposal for an annular gold dollar , that is , with a hole in the middle to increase its small diameter . McKay amended his legislation to provide for a double eagle ( $ 20 gold coin ) and wrote to Patterson , who replied stating that the annular gold dollar would not work , and neither would another proposal to have dollar piece consisting of a gold plug in a silver coin . Nevertheless , Gobrecht 's successor as chief engraver , James B. Longacre , prepared patterns , including some with a square hole in the middle .
|
[
3412,
878,
1248,
2780,
837,
1700,
6867,
286,
3869,
547,
17609,
284,
1605,
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284,
307,
7425,
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3561,
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7533,
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1529,
934,
3869,
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318,
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351,
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287,
262,
3504,
284,
2620,
663,
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37946,
11412,
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2148,
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1194,
6961,
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423,
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3704,
17747,
286,
257,
3869,
6107,
287,
257,
8465,
10752,
764,
15933,
837,
16909,
260,
21474,
705,
82,
17270,
355,
4039,
1786,
430,
332,
837,
3700,
347,
13,
5882,
12345,
837,
5597,
7572,
837,
1390,
617,
351,
257,
6616,
7604,
287,
262,
3504,
764,
220,
198
] |
McKay got his fellow Democrat , New Hampshire Senator Charles Atherton , to introduce the bill to authorize the gold dollar and the double eagle in the Senate on February 1 , 1849 — Atherton was chairman of the Senate Finance Committee . McKay introduced a version into the House on February 20 ; debate began the same day . The dollar was attacked by congressmen from the Whig Party , then in the minority , on the grounds that it would be too small , would be counterfeited and in bad light might be mistakenly spent as a half dime , the coins being similar in size . McKay did not respond substantively , but stated that if no one wanted these denominations , they would not be called for at the Mint , and would not be coined . Pennsylvania Representative Joseph Ingersoll , a Whig , spoke against the bill , noting that Patterson opposed the new denominations , and that the idea had been repeatedly turned down , whenever considered . Another Whig , Massachusetts 's Charles Hudson , related that Patterson had sent a real and a counterfeit gold dollar to his committee and the majority of members had been unable to tell the difference . McKay made no answer to these claims , but others did , including New York Congressman Henry Nicoll , who assured the House that the counterfeiting allegations were greatly exaggerated . The point was , he indicated , that the double eagle and gold dollar were wanted by the public , and , in the case of the gold dollar could help money circulate in small communities where banknotes were not accepted . Connecticut Representative John A. Rockwell , a Whig , tried to table the bill , but his motion was defeated . The bill passed easily , and met only minimal opposition in the Senate , becoming law on March 3 , 1849 .
|
[
37946,
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7212,
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692,
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257,
854,
328,
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5158,
1028,
262,
2855,
837,
10820,
326,
27042,
6886,
262,
649,
49735,
837,
290,
326,
262,
2126,
550,
587,
7830,
2900,
866,
837,
8797,
3177,
764,
6023,
854,
328,
837,
10140,
705,
82,
7516,
19995,
837,
3519,
326,
27042,
550,
1908,
257,
1103,
290,
257,
36497,
3869,
8872,
284,
465,
5583,
290,
262,
3741,
286,
1866,
550,
587,
5906,
284,
1560,
262,
3580,
764,
37946,
925,
645,
3280,
284,
777,
3667,
837,
475,
1854,
750,
837,
1390,
968,
1971,
30700,
8616,
8377,
692,
837,
508,
13933,
262,
2097,
326,
262,
29465,
1780,
7636,
547,
9257,
25291,
764,
383,
966,
373,
837,
339,
8203,
837,
326,
262,
4274,
31176,
290,
3869,
8872,
547,
2227,
416,
262,
1171,
837,
290,
837,
287,
262,
1339,
286,
262,
3869,
8872,
714,
1037,
1637,
49306,
287,
1402,
5348,
810,
3331,
17815,
547,
407,
6292,
764,
14493,
19920,
1757,
317,
13,
4631,
4053,
837,
257,
854,
328,
837,
3088,
284,
3084,
262,
2855,
837,
475,
465,
6268,
373,
9772,
764,
383,
2855,
3804,
3538,
837,
290,
1138,
691,
10926,
5471,
287,
262,
3845,
837,
5033,
1099,
319,
2805,
513,
837,
1248,
2920,
764,
220,
198
] |
= = Preparation = =
|
[
796,
796,
38397,
341,
796,
796,
220,
198
] |
The officers at the Philadelphia Mint , including Chief Coiner Franklin Peale , were mostly the friends and relations of Director Patterson . The outsider in their midst was Chief Engraver James B. Longacre , successor to Gobrecht ( who had died in 1844 ) . A former copper @-@ plate engraver , Longacre had been appointed through the political influence of South Carolina Senator John C. Calhoun .
|
[
383,
3790,
379,
262,
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5953,
1766,
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14021,
2631,
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837,
547,
4632,
262,
2460,
290,
2316,
286,
5890,
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383,
30545,
287,
511,
15925,
373,
5953,
1985,
430,
332,
3700,
347,
13,
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12345,
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284,
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21474,
357,
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3724,
287,
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2598,
1267,
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317,
1966,
15317,
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12,
31,
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550,
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9899,
832,
262,
1964,
4588,
286,
2520,
5913,
8962,
1757,
327,
13,
2199,
47714,
764,
220,
198
] |
When Longacre began work on the two new coins in early 1849 , he had no one to assist him . Longacre wrote the following year that he had been warned by a Mint employee that one of the officers ( undoubtedly Peale ) planned to undermine the chief engraver 's position by having the work of preparing designs and dies done outside Mint premises . Accordingly , when the gold coin bill became law , Longacre apprised Patterson that he was ready to begin work on the gold dollar . The Mint Director agreed , and after viewing a model of the head on the obverse , authorized Longacre to proceed with preparation of dies . According to Longacre ,
|
[
1649,
5882,
12345,
2540,
670,
319,
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17095,
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28386,
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618,
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2855,
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598,
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1417,
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373,
3492,
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2221,
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319,
262,
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764,
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20873,
5890,
4987,
837,
290,
706,
11681,
257,
2746,
286,
262,
1182,
319,
262,
909,
4399,
837,
10435,
5882,
12345,
284,
5120,
351,
11824,
286,
10564,
764,
4784,
284,
5882,
12345,
837,
220,
198
] |
The engraving was unusually minute and required very close and incessant labor for several weeks . I made the original dies and hubs for making the working dies twice over , to secure their perfect adaptation to the coining machinery . I had a wish to execute this work single handed , that I might thus silently reply to those who had questioned my ability for the work . The result , I believe , was satisfactory .
|
[
383,
1786,
430,
1075,
373,
23708,
5664,
290,
2672,
845,
1969,
290,
41106,
415,
4827,
329,
1811,
2745,
764,
314,
925,
262,
2656,
10564,
290,
38459,
329,
1642,
262,
1762,
10564,
5403,
625,
837,
284,
5713,
511,
2818,
16711,
284,
262,
763,
3191,
20230,
764,
314,
550,
257,
4601,
284,
12260,
428,
670,
2060,
10158,
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326,
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1244,
4145,
24595,
10971,
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883,
508,
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11434,
616,
2694,
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262,
670,
764,
383,
1255,
837,
314,
1975,
837,
373,
29962,
764,
220,
198
] |
= = Original design = =
|
[
796,
796,
13745,
1486,
796,
796,
220,
198
] |
The Type 1 gold dollar depicts a head of Liberty , facing left , with a coronet or tiara on her head bearing her name . Her hair is gathered in a bun ; she is surrounded by 13 stars representing the original states . The reverse features the date and denomination within a wreath , with the name of the nation near the rim .
|
[
383,
5994,
352,
3869,
8872,
28539,
257,
1182,
286,
14734,
837,
6476,
1364,
837,
351,
257,
26920,
316,
393,
46668,
3301,
319,
607,
1182,
14121,
607,
1438,
764,
2332,
4190,
318,
9272,
287,
257,
28773,
2162,
673,
318,
11191,
416,
1511,
5788,
10200,
262,
2656,
2585,
764,
383,
9575,
3033,
262,
3128,
290,
47491,
1626,
257,
266,
19367,
837,
351,
262,
1438,
286,
262,
3277,
1474,
262,
20254,
764,
220,
198
] |
Contemporary reviews of the Type 1 design were generally favorable . The New York Weekly Tribune on May 19 , 1849 described the new dollar as " undoubtedly the neatest , tiniest , lightest , coin in this country ... it is too delicate and beautiful to pay out for potatoes , and sauerkraut , and salt pork . Oberon might have paid Puck with it for bringing the blossom which bewitched Titania . " Willis ' Bank Note List stated that " there is no probability of them ever getting into general circulation ; they are altogether too small . " The North Carolina Standard hoped that they would be struck at the Charlotte Mint and circulated locally to eliminate the problem of small @-@ denomination bank notes from out of state . Coin dealer and numismatic author Q. David Bowers notes that the head of Liberty on the Type 1 dollar is a scaled @-@ down version of that on the double eagle , and " a nicely preserved gold dollar is beautiful to behold " .
|
[
38698,
8088,
286,
262,
5994,
352,
1486,
547,
4143,
17070,
764,
383,
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18168,
17588,
319,
1737,
678,
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1248,
2920,
3417,
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17713,
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256,
5362,
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428,
1499,
2644,
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1165,
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612,
318,
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12867,
286,
606,
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1972,
656,
2276,
19133,
2162,
484,
389,
13318,
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1402,
764,
366,
383,
2258,
5913,
8997,
10719,
326,
484,
561,
307,
7425,
379,
262,
14685,
20873,
290,
26772,
15726,
284,
11005,
262,
1917,
286,
1402,
2488,
12,
31,
47491,
3331,
4710,
422,
503,
286,
1181,
764,
16312,
16456,
290,
997,
1042,
1512,
1772,
1195,
13,
3271,
347,
3618,
4710,
326,
262,
1182,
286,
14734,
319,
262,
5994,
352,
8872,
318,
257,
27464,
2488,
12,
31,
866,
2196,
286,
326,
319,
262,
4274,
31176,
837,
290,
366,
257,
16576,
17232,
3869,
8872,
318,
4950,
284,
23700,
366,
764,
220,
198
] |
= = Modifications = =
|
[
796,
796,
3401,
6637,
796,
796,
220,
198
] |
Mint records indicate the first gold dollars were produced on May 7 , 1849 ; Longacre 's diary notes state instead that the first were struck on May 8 . A few coins in proof condition were struck on the first day , along with about 1 @,@ 000 for circulation . There are five major varieties of the 1849 gold dollar from Philadelphia , made as Longacre continued to fine @-@ tune the design . <unk> dies were sent by Longacre 's Engraving Department at the Philadelphia Mint to the branch mints at Charlotte , Dahlonega ( in Georgia ) , and New Orleans ; coins struck at the branches resemble some of the types issued from Philadelphia , depending on when the dies were produced . Of the coins struck at the branch mints in 1849 , only pieces struck at Charlotte ( 1849 @-@ C ) exist in multiple varieties ; most are of what is dubbed the " Closed Wreath " variety . Approximately five of the 1849 @-@ C Open Wreath are known ; one , believed the finest surviving specimen , sold at auction for $ 690 @,@ 000 in 2004 , remaining a record for the gold dollar series as of 2013 . One of the changes made during production was the inclusion of Longacre 's initial " L " on the truncation of Liberty 's neck , the first time a U.S. coin intended for full @-@ scale production had borne the initial of its designer . All issues beginning in 1850 bear the Closed Wreath . Beginning in 1854 , the gold dollar was also struck at the new San Francisco Mint .
|
[
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718,
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2168,
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3227,
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640,
257,
471,
13,
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13,
10752,
5292,
329,
1336,
2488,
12,
31,
5046,
3227,
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4238,
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2428,
3726,
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19367,
764,
25976,
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1248,
4051,
837,
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3869,
8872,
373,
635,
7425,
379,
262,
649,
2986,
6033,
20873,
764,
220,
198
] |
The continued flow of gold from California made silver expensive in terms of gold , and U.S. silver coins began to flow out of the country for melting in 1849 , a flow that accelerated over the next several years as the price of the metal continued to rise . By 1853 , a thousand dollars in silver coin contained $ 1 @,@ 042 worth of bullion . As silver coins vanished , the gold dollar became the only federal coin in circulation between the cent and the quarter eagle ( $ 2 @.@ 50 piece ) . As such , it was struck in large numbers and widely circulated . According to Bowers in his book on the denomination , " the years 1850 to 1853 were the high @-@ water mark of the gold dollar , the glory years of the denomination when the little gold coins took the place of half dollars and silver dollars in everyday transactions . " This time came to an end in 1853 when Congress passed an act reducing the weight of most silver coins , allowing new issues of them to circulate .
|
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4310,
618,
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3804,
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286,
749,
8465,
10796,
837,
5086,
649,
2428,
286,
606,
284,
49306,
764,
220,
198
] |
As early as 1851 , New York Congressman William Duer alleged that that Patterson had made the gold dollar too small in diameter on purpose to provoke criticism . Patterson retired that year after 16 years in his position , and under his successor , George N. Eckert , annular gold dollar and half dollar patterns were struck . Public Ledger reported that although gold dollars would not be struck in annular form , gold half dollars would be , to help fill the need for change . With the new Pierce administration , Thomas M. Pettit took office as Mint Director on March 31 , 1853 . In April , Treasury Secretary James Guthrie wrote to Pettit that there were complaints that the gold dollar was too small , often lost or mistaken for a small silver coin , and enquiring about reports the Mint had experimented with annular dollars . Pettit replied , stating that none had been preserved , but enclosed a silver piece of equivalent size . He noted that while there would be technical difficulties in the production of the annular dollar , these could be overcome . In a letter dated May 10 , Pettit proposed an oval @-@ shaped holed piece , or an angular @-@ shaped coin , which would lessen the production problems . Pettit died suddenly on May 31 ; Guthrie did not let the issue fall , but queried Pettit 's replacement , James Ross Snowden , concerning the issue on June 7 . As U.S. coins were required to bear some device emblematic of liberty , the secretary hoped that artists could be found who could find some such design for an annular coin .
|
[
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326,
612,
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262,
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2626,
393,
16011,
329,
257,
1402,
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290,
34593,
3428,
546,
3136,
262,
20873,
550,
42107,
351,
1529,
934,
5054,
764,
35043,
270,
8712,
837,
12316,
326,
4844,
550,
587,
17232,
837,
475,
28543,
257,
8465,
3704,
286,
7548,
2546,
764,
679,
4367,
326,
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612,
561,
307,
6276,
13156,
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262,
3227,
286,
262,
1529,
934,
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777,
714,
307,
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764,
554,
257,
3850,
14567,
1737,
838,
837,
35043,
270,
5150,
281,
41186,
2488,
12,
31,
14292,
6039,
276,
3704,
837,
393,
281,
32558,
2488,
12,
31,
14292,
10752,
837,
543,
561,
40856,
262,
3227,
2761,
764,
35043,
270,
3724,
6451,
319,
1737,
3261,
2162,
44003,
5034,
750,
407,
1309,
262,
2071,
2121,
837,
475,
42517,
798,
35043,
270,
705,
82,
9014,
837,
3700,
9847,
15015,
837,
9305,
262,
2071,
319,
2795,
767,
764,
1081,
471,
13,
50,
13,
10796,
547,
2672,
284,
6842,
617,
3335,
32094,
1512,
286,
12354,
837,
262,
7705,
10719,
326,
7912,
714,
307,
1043,
508,
714,
1064,
617,
884,
1486,
329,
281,
1529,
934,
10752,
764,
220,
198
] |
The Act of February 21 , 1853 , that had lightened the silver coins also authorized a gold three @-@ dollar piece , which began to be produced in 1854 . To ensure that the three @-@ dollar piece was not mistaken for other gold coins , it had been made thinner and wider than it would normally be , and Longacre put a distinctive design with an Indian princess on it . Longacre adapted both the technique and the design for the gold dollar , which was made thinner , and thus wider . An adaptation of Longacre 's princess for the larger gold coin was placed on the dollar , and a similar agricultural wreath on the reverse . The idea of making the gold dollar larger in this way had been suggested in Congress as early as 1852 , and had been advocated by Pettit , but Guthrie 's desire for an annular coin stalled the matter . In May 1854 , Snowden sent Guthrie a letter stating that the difficulties with an annular coin , especially in getting the coins to eject properly from the press , were more than trivial .
|
[
383,
2191,
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635,
10435,
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31,
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2540,
284,
307,
4635,
287,
1248,
4051,
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1675,
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257,
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3942,
21752,
319,
340,
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1111,
262,
8173,
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262,
1486,
329,
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30125,
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1052,
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329,
262,
4025,
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10752,
373,
4624,
319,
262,
8872,
837,
290,
257,
2092,
14240,
266,
19367,
319,
262,
9575,
764,
383,
2126,
286,
1642,
262,
3869,
8872,
4025,
287,
428,
835,
550,
587,
5220,
287,
3162,
355,
1903,
355,
1248,
4309,
837,
290,
550,
587,
25828,
416,
35043,
270,
837,
475,
44003,
5034,
705,
82,
6227,
329,
281,
1529,
934,
10752,
29759,
262,
2300,
764,
554,
1737,
1248,
4051,
837,
15015,
1908,
44003,
5034,
257,
3850,
12316,
326,
262,
13156,
351,
281,
1529,
934,
10752,
837,
2592,
287,
1972,
262,
10796,
284,
22189,
6105,
422,
262,
1803,
837,
547,
517,
621,
20861,
764,
220,
198
] |
Nevertheless , the Type 2 gold dollar ( as it came to be known ) proved unsatisfactory as the mints had difficulty in striking the new coin so that all details were brought out . This was due to the high relief of the design — the three Southern branch mints especially had trouble with the piece . Many of the Type 2 pieces quickly became illegible , and were sent back to Philadelphia for melting and recoinage . On most surviving specimens , the " 85 " in the date is not fully detailed . The Type 2 gold dollar was struck only at Philadelphia in 1854 and 1855 , at the three Southern branch mints in the latter year , and at San Francisco in 1856 , after the design was designated for replacement . To correct the problems , Longacre enlarged the head of Liberty , making it a scaled @-@ down version of the three @-@ dollar piece , and moved the lettering on the obverse closer to the rim . This improved the metal flow and design sharpness so much that early numismatic scholars assumed the reverse was also altered , though in fact no change was made and the Type 2 and Type 3 reverses are identical .
|
[
15933,
837,
262,
5994,
362,
3869,
8872,
357,
355,
340,
1625,
284,
307,
1900,
1267,
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39264,
9548,
355,
262,
21043,
82,
550,
8722,
287,
8871,
262,
649,
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523,
326,
477,
3307,
547,
3181,
503,
764,
770,
373,
2233,
284,
262,
1029,
8259,
286,
262,
1486,
851,
262,
1115,
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496,
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749,
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262,
366,
7600,
366,
287,
262,
3128,
318,
407,
3938,
6496,
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383,
5994,
362,
3869,
8872,
373,
7425,
691,
379,
8857,
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1248,
4051,
290,
1248,
2816,
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379,
262,
1115,
8050,
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21043,
82,
287,
262,
6846,
614,
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290,
379,
2986,
6033,
287,
1248,
3980,
837,
706,
262,
1486,
373,
11032,
329,
9014,
764,
1675,
3376,
262,
2761,
837,
5882,
12345,
37287,
262,
1182,
286,
14734,
837,
1642,
340,
257,
27464,
2488,
12,
31,
866,
2196,
286,
262,
1115,
2488,
12,
31,
8872,
3704,
837,
290,
3888,
262,
3850,
278,
319,
262,
909,
4399,
5699,
284,
262,
20254,
764,
770,
6596,
262,
6147,
5202,
290,
1486,
7786,
1108,
523,
881,
326,
1903,
997,
1042,
1512,
9123,
9672,
262,
9575,
373,
635,
14294,
837,
996,
287,
1109,
645,
1487,
373,
925,
290,
262,
5994,
362,
290,
5994,
513,
10372,
274,
389,
10411,
764,
220,
198
] |
= = = Design of Type 2 and 3 dollars = = =
|
[
796,
796,
796,
8495,
286,
5994,
362,
290,
513,
5054,
796,
796,
796,
220,
198
] |
The Type 2 and 3 gold dollars depict Liberty as a Native American princess , with a fanciful feathered headdress not resembling any worn by any Indian tribe . This image is an inexact copy of the design Longacre had made for the three @-@ dollar piece , and is one of a number of versions of Liberty Longacre created based on the Venus <unk> or Crouching Venus , a sculpture then on display in a Philadelphia museum . For the reverse , Longacre adapted the " agricultural wreath " he had created for the reverse of the three @-@ dollar piece , composed of cotton , corn , tobacco , and wheat , blending the produce of North and South . This wreath would appear , later in the 1850s , on the Flying Eagle cent .
|
[
383,
5994,
362,
290,
513,
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39980,
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1912,
319,
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21094,
1279,
2954,
29,
393,
327,
472,
10813,
21094,
837,
257,
26924,
788,
319,
3359,
287,
257,
8857,
13257,
764,
1114,
262,
9575,
837,
5882,
12345,
16573,
262,
366,
14240,
266,
19367,
366,
339,
550,
2727,
329,
262,
9575,
286,
262,
1115,
2488,
12,
31,
8872,
3704,
837,
13160,
286,
15985,
837,
11676,
837,
11219,
837,
290,
17135,
837,
34863,
262,
4439,
286,
2258,
290,
2520,
764,
770,
266,
19367,
561,
1656,
837,
1568,
287,
262,
35745,
82,
837,
319,
262,
19903,
18456,
1247,
764,
220,
198
] |
Art historian Cornelius Vermeule deprecated the Indian princess design used by Longacre for the obverses of the Types 2 and 3 gold dollar , and for the three @-@ dollar piece , " the ' princess ' of the gold coins is a banknote engraver 's elegant version of folk art of the 1850s . The plumes or feathers are more like the crest of the Prince of Wales than anything that saw the Western frontiers , save perhaps on a music hall beauty . "
|
[
3683,
18026,
48214,
3754,
4643,
1326,
2261,
39224,
262,
3942,
21752,
1486,
973,
416,
5882,
12345,
329,
262,
909,
690,
274,
286,
262,
24897,
362,
290,
513,
3869,
8872,
837,
290,
329,
262,
1115,
2488,
12,
31,
8872,
3704,
837,
366,
262,
705,
21752,
705,
286,
262,
3869,
10796,
318,
257,
3331,
11295,
1786,
430,
332,
705,
82,
19992,
2196,
286,
15504,
1242,
286,
262,
35745,
82,
764,
383,
458,
8139,
393,
27400,
389,
517,
588,
262,
36893,
286,
262,
9005,
286,
11769,
621,
1997,
326,
2497,
262,
4885,
2166,
3183,
837,
3613,
3737,
319,
257,
2647,
6899,
8737,
764,
366,
220,
198
] |
= = War years = =
|
[
796,
796,
1810,
812,
796,
796,
220,
198
] |
The gold dollar continued to be produced in the late 1850s , though mintages declined from the figures of two million or more each year between 1850 and 1854 . Only about 51 @,@ 000 gold dollars were produced in 1860 , with over two @-@ thirds of that figure at Philadelphia , just under a third at San Francisco , and 1 @,@ 566 at Dahlonega . Roughly a hundred are known of the last , creating one of the great rarities from Dahlonega in the series .
|
[
383,
3869,
8872,
3767,
284,
307,
4635,
287,
262,
2739,
35745,
82,
837,
996,
21043,
1095,
7392,
422,
262,
5538,
286,
734,
1510,
393,
517,
1123,
614,
1022,
35745,
290,
1248,
4051,
764,
5514,
546,
6885,
2488,
11,
31,
12877,
3869,
5054,
547,
4635,
287,
37637,
837,
351,
625,
734,
2488,
12,
31,
41188,
286,
326,
3785,
379,
8857,
837,
655,
739,
257,
2368,
379,
2986,
6033,
837,
290,
352,
2488,
11,
31,
642,
2791,
379,
41471,
505,
4908,
764,
29949,
306,
257,
3470,
389,
1900,
286,
262,
938,
837,
4441,
530,
286,
262,
1049,
374,
283,
871,
422,
41471,
505,
4908,
287,
262,
2168,
764,
220,
198
] |
The other candidate for the rarest from that mint is the 1861 @-@ D , with an estimated mintage of 1 @,@ 000 and perhaps 45 to 60 known . Two pairs of dies were shipped from Philadelphia to Dahlonega on December 10 , 1860 ; they arrived on January 7 , 1861 , two weeks before Georgia voted to secede from the Union , as the American Civil War began . Under orders from Governor Joseph E. Brown , state militia secured the mint , and at some point , small quantities of dollars and half eagles were produced . Records of how many coins were struck and when have not survived . Since dies crack in time , and all the mints were supplied with them from Philadelphia , coining could not last , and in May 1861 , coins and supplies remaining at Dahlonega were turned over to the treasury of the Confederate States of America , which Georgia had by then joined . Gold coins with a face value of $ 6 were put aside for assay . Normally , they would have been sent to Philadelphia to await the following year 's meeting of the United States Assay Commission , when they would be available for testing . Instead , these were sent to the initial Confederate capital of Montgomery , Alabama , though what was done with them there , and their ultimate fate , are unknown . The rarity of the 1861 @-@ D dollar , and the association with the Confederacy , make it especially prized .
|
[
383,
584,
4540,
329,
262,
4071,
301,
422,
326,
21043,
318,
262,
45278,
2488,
12,
31,
360,
837,
351,
281,
6108,
285,
14630,
286,
352,
2488,
11,
31,
12877,
290,
3737,
4153,
284,
3126,
1900,
764,
4930,
14729,
286,
10564,
547,
14338,
422,
8857,
284,
41471,
505,
4908,
319,
3426,
838,
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37637,
2162,
484,
5284,
319,
3269,
767,
837,
45278,
837,
734,
2745,
878,
7859,
7052,
284,
384,
771,
68,
422,
262,
4479,
837,
355,
262,
1605,
7511,
1810,
2540,
764,
4698,
6266,
422,
10807,
7212,
412,
13,
4373,
837,
1181,
21085,
13659,
262,
21043,
837,
290,
379,
617,
966,
837,
1402,
17794,
286,
5054,
290,
2063,
304,
37803,
547,
4635,
764,
13407,
286,
703,
867,
10796,
547,
7425,
290,
618,
423,
407,
11803,
764,
4619,
10564,
8469,
287,
640,
837,
290,
477,
262,
21043,
82,
547,
14275,
351,
606,
422,
8857,
837,
763,
3191,
714,
407,
938,
837,
290,
287,
1737,
45278,
837,
10796,
290,
9416,
5637,
379,
41471,
505,
4908,
547,
2900,
625,
284,
262,
38115,
286,
262,
21900,
1829,
286,
2253,
837,
543,
7859,
550,
416,
788,
5399,
764,
3561,
10796,
351,
257,
1986,
1988,
286,
720,
718,
547,
1234,
7263,
329,
40575,
764,
29282,
837,
484,
561,
423,
587,
1908,
284,
8857,
284,
25507,
262,
1708,
614,
705,
82,
3249,
286,
262,
1578,
1829,
2195,
323,
4513,
837,
618,
484,
561,
307,
1695,
329,
4856,
764,
5455,
837,
777,
547,
1908,
284,
262,
4238,
21900,
3139,
286,
21532,
837,
9266,
837,
996,
644,
373,
1760,
351,
606,
612,
837,
290,
511,
8713,
10030,
837,
389,
6439,
764,
383,
32823,
286,
262,
45278,
2488,
12,
31,
360,
8872,
837,
290,
262,
8112,
351,
262,
45252,
837,
787,
340,
2592,
37768,
764,
220,
198
] |
Dahlonega , like the other two branch mints in the South , closed its doors after the 1861 strikings . It and the Charlotte facility never reopened ; the New Orleans Mint again struck coins from 1879 to 1909 , but did not strike gold dollars again . After 1861 , the only issuance of gold dollars outside Philadelphia was at San Francisco , in 1870 .
|
[
41471,
505,
4908,
837,
588,
262,
584,
734,
8478,
21043,
82,
287,
262,
2520,
837,
4838,
663,
8215,
706,
262,
45278,
2338,
74,
654,
764,
632,
290,
262,
14685,
6841,
1239,
37415,
2162,
262,
968,
12255,
20873,
757,
7425,
10796,
422,
1248,
3720,
284,
41507,
837,
475,
750,
407,
5587,
3869,
5054,
757,
764,
2293,
45278,
837,
262,
691,
30145,
286,
3869,
5054,
2354,
8857,
373,
379,
2986,
6033,
837,
287,
37667,
764,
220,
198
] |
The outbreak of the Civil War shook public confidence in the Union , and citizens began hoarding specie , gold and silver coins . In late December 1861 , banks and then the federal Treasury stopped paying out gold at face value . By mid @-@ 1862 , all federal coins , even the base metal cent , had vanished from commerce in much of the country . The exception was the Far West , where for the most part , only gold and silver were acceptable currencies , and paper money traded at a discount . In the rest of the nation , gold and silver coins could be purchased from banks , exchange agents , and from the Treasury for a premium in the new greenbacks the government began to issue to fill the gap in commerce and finance the war .
|
[
383,
17645,
286,
262,
7511,
1810,
14682,
1171,
6628,
287,
262,
4479,
837,
290,
4290,
2540,
8169,
13493,
1020,
494,
837,
3869,
290,
8465,
10796,
764,
554,
2739,
3426,
45278,
837,
6341,
290,
788,
262,
2717,
13419,
5025,
5989,
503,
3869,
379,
1986,
1988,
764,
2750,
3095,
2488,
12,
31,
49658,
837,
477,
2717,
10796,
837,
772,
262,
2779,
6147,
1247,
837,
550,
23717,
422,
19497,
287,
881,
286,
262,
1499,
764,
383,
6631,
373,
262,
6755,
2688,
837,
810,
329,
262,
749,
636,
837,
691,
3869,
290,
8465,
547,
10909,
19247,
837,
290,
3348,
1637,
14018,
379,
257,
9780,
764,
554,
262,
1334,
286,
262,
3277,
837,
3869,
290,
8465,
10796,
714,
307,
8155,
422,
6341,
837,
5163,
6554,
837,
290,
422,
262,
13419,
329,
257,
8683,
287,
262,
649,
4077,
10146,
262,
1230,
2540,
284,
2071,
284,
6070,
262,
7625,
287,
19497,
290,
9604,
262,
1175,
764,
220,
198
] |
= = Final years , abolition , and collecting = =
|
[
796,
796,
8125,
812,
837,
30480,
837,
290,
13157,
796,
796,
220,
198
] |
Since gold did not circulate in the United States ( except on the West Coast ) in the postwar period , much of the production of coins of that metal in the United States was double eagles for export . Accordingly , although 1 @,@ 361 @,@ 355 gold dollars were struck in 1862 — the last time production would exceed a million — the mintage fell to 6 @,@ 200 in 1863 and remained low for the rest of the coin 's existence , excepting 1873 and 1874 . The Mint felt it improper to suspend coinage of a coin authorized by Congress , and issued proof coins ( generally a few dozen to the tiny numismatic community ) from specially @-@ polished dies , also producing enough circulation strikes so that the proof coins would not be unduly rare . In 1873 and 1874 , old and worn gold dollars held by the government were melted and recoined , generating large mintages of that denomination . This was done in anticipation of the resumption of specie payments , which did not occur until the end of 1878 . Once specie again circulated at face value , the gold dollar found no place in commerce amid large quantities of silver coinage , either released from hoarding or newly struck by the Mint . The government expected that the resumption of specie payments would cause the dollar and other small gold coins to circulate again , but the public , allowed to redeem paper currency , continued to use it as more convenient than coins .
|
[
4619,
3869,
750,
407,
49306,
287,
262,
1578,
1829,
357,
2845,
319,
262,
2688,
8545,
1267,
287,
262,
44060,
2278,
837,
881,
286,
262,
3227,
286,
10796,
286,
326,
6147,
287,
262,
1578,
1829,
373,
4274,
304,
37803,
329,
10784,
764,
28386,
837,
3584,
352,
2488,
11,
31,
47744,
2488,
11,
31,
36561,
3869,
5054,
547,
7425,
287,
49658,
851,
262,
938,
640,
3227,
561,
7074,
257,
1510,
851,
262,
285,
14630,
3214,
284,
718,
2488,
11,
31,
939,
287,
47072,
290,
6150,
1877,
329,
262,
1334,
286,
262,
10752,
705,
82,
6224,
837,
2845,
278,
1248,
4790,
290,
1248,
4524,
764,
383,
20873,
2936,
340,
18992,
284,
22004,
10752,
496,
286,
257,
10752,
10435,
416,
3162,
837,
290,
4884,
6617,
10796,
357,
4143,
257,
1178,
8667,
284,
262,
7009,
997,
1042,
1512,
2055,
1267,
422,
20905,
2488,
12,
31,
23895,
10564,
837,
635,
9194,
1576,
19133,
8956,
523,
326,
262,
6617,
10796,
561,
407,
307,
3318,
2062,
4071,
764,
554,
1248,
4790,
290,
1248,
4524,
837,
1468,
290,
12666,
3869,
5054,
2714,
416,
262,
1230,
547,
24178,
290,
664,
78,
1389,
837,
15453,
1588,
21043,
1095,
286,
326,
47491,
764,
770,
373,
1760,
287,
24054,
286,
262,
581,
24098,
286,
1020,
494,
7524,
837,
543,
750,
407,
3051,
1566,
262,
886,
286,
1248,
3695,
764,
4874,
1020,
494,
757,
26772,
379,
1986,
1988,
837,
262,
3869,
8872,
1043,
645,
1295,
287,
19497,
10371,
1588,
17794,
286,
8465,
10752,
496,
837,
2035,
2716,
422,
8169,
13493,
393,
8308,
7425,
416,
262,
20873,
764,
383,
1230,
2938,
326,
262,
581,
24098,
286,
1020,
494,
7524,
561,
2728,
262,
8872,
290,
584,
1402,
3869,
10796,
284,
49306,
757,
837,
475,
262,
1171,
837,
3142,
284,
26509,
3348,
7395,
837,
3767,
284,
779,
340,
355,
517,
11282,
621,
10796,
764,
220,
198
] |
In the 1870s and 1880s , public interest grew in the low @-@ mintage gold dollar . Collecting coins was becoming more popular , and a number of numismatists put aside some gold dollars and hoped for increases in value . The Mint most likely channeled its production through some favored Philadelphia dealers , though proof coins could be purchased for $ 1 @.@ 25 at the cashier 's window at the Philadelphia facility . Banks charged a premium for circulation strikes . They were popular in the jewelry trade , mounted into various items . The coins were often exported to China or Japan , where such jewelry was made . The dollars were often damaged in the process ; the Mint refused to sell into this trade and did its best to hinder it . Nevertheless , Mint officials concluded that jewelers were successful at getting the majority of each issue . Proof mintages exceeded 1 @,@ 000 by 1884 , and remained above that mark for the remainder of the series , numbers likely inflated by agents of jewelers , willing to pay the Mint 's premium of $ .25 per coin . Another use for the gold dollar was as a holiday gift ; after its abolition the quarter eagle became a popular present .
|
[
554,
262,
37667,
82,
290,
34865,
82,
837,
1171,
1393,
6348,
287,
262,
1877,
2488,
12,
31,
285,
14630,
3869,
8872,
764,
9745,
278,
10796,
373,
5033,
517,
2968,
837,
290,
257,
1271,
286,
997,
1042,
265,
1023,
1234,
7263,
617,
3869,
5054,
290,
10719,
329,
5732,
287,
1988,
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383,
20873,
749,
1884,
6518,
276,
663,
3227,
832,
617,
19344,
8857,
15737,
837,
996,
6617,
10796,
714,
307,
8155,
329,
720,
352,
2488,
13,
31,
1679,
379,
262,
5003,
959,
705,
82,
4324,
379,
262,
8857,
6841,
764,
19566,
5047,
257,
8683,
329,
19133,
8956,
764,
1119,
547,
2968,
287,
262,
22634,
3292,
837,
12623,
656,
2972,
3709,
764,
383,
10796,
547,
1690,
29050,
284,
2807,
393,
2869,
837,
810,
884,
22634,
373,
925,
764,
383,
5054,
547,
1690,
9694,
287,
262,
1429,
2162,
262,
20873,
6520,
284,
3677,
656,
428,
3292,
290,
750,
663,
1266,
284,
34541,
340,
764,
15933,
837,
20873,
2828,
8391,
326,
16927,
364,
547,
4388,
379,
1972,
262,
3741,
286,
1123,
2071,
764,
29999,
21043,
1095,
20672,
352,
2488,
11,
31,
12877,
416,
1248,
5705,
837,
290,
6150,
2029,
326,
1317,
329,
262,
17675,
286,
262,
2168,
837,
3146,
1884,
32387,
416,
6554,
286,
16927,
364,
837,
4684,
284,
1414,
262,
20873,
705,
82,
8683,
286,
720,
764,
1495,
583,
10752,
764,
6023,
779,
329,
262,
3869,
8872,
373,
355,
257,
9912,
6979,
2162,
706,
663,
30480,
262,
3860,
31176,
2627,
257,
2968,
1944,
764,
220,
198
] |
James Pollock , in his final report as Mint Director in 1873 , advocated limiting striking of gold dollars to depositors who specifically requested it . " The gold dollar is not a convenient coin , on account of its small size , and it suffers more proportionately from abrasion than larger coins . " His successors called for its abolition , with James P. Kimball , before he left office in 1889 , writing to Congress that except as jewelry , " little practical use has been found for this coin " . Later that year , the new director , Edward O. Leech , issued a report stating that the gold dollar " is too small for circulation , and ... [ is ] used almost exclusively for the purposes of ornament . The last year in which the gold dollar was struck was 1889 . Congress abolished the gold dollar , along with the three @-@ cent nickel and three @-@ dollar piece , by the Act of September 26 , 1890 .
|
[
3700,
12868,
735,
837,
287,
465,
2457,
989,
355,
20873,
5890,
287,
1248,
4790,
837,
25828,
15637,
8871,
286,
3869,
5054,
284,
12304,
6742,
508,
5734,
9167,
340,
764,
366,
383,
3869,
8872,
318,
407,
257,
11282,
10752,
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319,
1848,
286,
663,
1402,
2546,
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290,
340,
21046,
517,
9823,
1286,
422,
450,
81,
4247,
621,
4025,
10796,
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2399,
41491,
1444,
329,
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30480,
837,
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3700,
350,
13,
6502,
1894,
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878,
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2607,
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49545,
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3162,
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22634,
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1310,
8472,
779,
468,
587,
1043,
329,
428,
10752,
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764,
11450,
326,
614,
837,
262,
649,
3437,
837,
10443,
440,
13,
1004,
3055,
837,
4884,
257,
989,
12316,
326,
262,
3869,
8872,
366,
318,
1165,
1402,
329,
19133,
837,
290,
2644,
685,
318,
2361,
973,
2048,
11541,
329,
262,
4959,
286,
45618,
764,
383,
938,
614,
287,
543,
262,
3869,
8872,
373,
7425,
373,
49545,
764,
3162,
32424,
262,
3869,
8872,
837,
1863,
351,
262,
1115,
2488,
12,
31,
1247,
30666,
290,
1115,
2488,
12,
31,
8872,
3704,
837,
416,
262,
2191,
286,
2693,
2608,
837,
31982,
764,
220,
198
] |
A total of 19 @,@ 499 @,@ 337 gold dollars were coined , of which 18 @,@ 223 @,@ 438 were struck at Philadelphia , 1 @,@ 004 @,@ 000 at New Orleans , 109 @,@ 138 at Charlotte , 90 @,@ 232 at San Francisco and 72 @,@ 529 at Dahlonega . According to an advertisement in the February 1899 issue of The Numismatist , gold dollars brought $ 1 @.@ 80 each , still in demand as a birthday present and for jewelry . That journal in 1905 carried news of a customer depositing 100 gold dollars into a bank ; the teller , aware of the value , credited the account with $ 1 @.@ 60 per coin . In 1908 , a dealer offered $ 2 each for any quantity . As coin collecting became a widespread pastime in the early 20th century , gold dollars became a popular specialty , a status they retain . The 2014 edition of R.S. Yeoman 's A Guide Book of United States Coins rates the least expensive gold dollar in very fine condition ( VF @-@ 20 ) at $ 300 , a value given for each of the Type 1 Philadelphia issues from 1849 to 1853 . Those seeking one of each type will find the most expensive to be a specimen of the Type 2 , with the 1854 and 1855 estimated at $ 350 in that condition ; the other two types have dates valued at $ 300 in that grade .
|
[
317,
2472,
286,
678,
2488,
11,
31,
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2488,
11,
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42294,
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5054,
547,
33115,
837,
286,
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1248,
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11,
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604,
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286,
383,
31835,
1042,
265,
396,
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3869,
5054,
3181,
720,
352,
2488,
13,
31,
4019,
1123,
837,
991,
287,
3512,
355,
257,
10955,
1944,
290,
329,
22634,
764,
1320,
3989,
287,
37166,
5281,
1705,
286,
257,
6491,
12304,
1780,
1802,
3869,
5054,
656,
257,
3331,
2162,
262,
1560,
263,
837,
3910,
286,
262,
1988,
837,
18141,
262,
1848,
351,
720,
352,
2488,
13,
31,
3126,
583,
10752,
764,
554,
40417,
837,
257,
16456,
4438,
720,
362,
1123,
329,
597,
12040,
764,
1081,
10752,
13157,
2627,
257,
10095,
1613,
524,
287,
262,
1903,
1160,
400,
4289,
837,
3869,
5054,
2627,
257,
2968,
22847,
837,
257,
3722,
484,
12377,
764,
383,
1946,
8313,
286,
371,
13,
50,
13,
11609,
5185,
705,
82,
317,
10005,
4897,
286,
1578,
1829,
30108,
3965,
262,
1551,
5789,
3869,
8872,
287,
845,
3734,
4006,
357,
569,
37,
2488,
12,
31,
1160,
1267,
379,
720,
5867,
837,
257,
1988,
1813,
329,
1123,
286,
262,
5994,
352,
8857,
2428,
422,
1248,
2920,
284,
1248,
4310,
764,
5845,
6095,
530,
286,
1123,
2099,
481,
1064,
262,
749,
5789,
284,
307,
257,
31674,
286,
262,
5994,
362,
837,
351,
262,
1248,
4051,
290,
1248,
2816,
6108,
379,
720,
13803,
287,
326,
4006,
2162,
262,
584,
734,
3858,
423,
9667,
17560,
379,
720,
5867,
287,
326,
9559,
764,
220,
198
] |
= = Commemorative gold dollars = =
|
[
796,
796,
1520,
368,
36478,
3869,
5054,
796,
796,
220,
198
] |
The gold dollar had a brief resurrection during the period of Early United States commemorative coins . Between 1903 and 1922 nine different issues were produced , with a total mintage of 99 @,@ 799 . These were minted for various public events , did not circulate , and none used Longacre 's design .
|
[
383,
3869,
8872,
550,
257,
4506,
27556,
1141,
262,
2278,
286,
12556,
1578,
1829,
28723,
876,
10796,
764,
14307,
41625,
290,
36094,
5193,
1180,
2428,
547,
4635,
837,
351,
257,
2472,
285,
14630,
286,
7388,
2488,
11,
31,
767,
2079,
764,
2312,
547,
21043,
276,
329,
2972,
1171,
2995,
837,
750,
407,
49306,
837,
290,
4844,
973,
5882,
12345,
705,
82,
1486,
764,
220,
198
] |
= Johnson – Corey – Chaykovsky reaction =
|
[
796,
5030,
784,
24154,
784,
609,
323,
21862,
15688,
6317,
796,
220,
198
] |
The Johnson – Corey – Chaykovsky reaction ( sometimes referred to as the Corey – Chaykovsky reaction or CCR ) is a chemical reaction used in organic chemistry for the synthesis of epoxides , aziridines , and <unk> . It was discovered in 1961 by A. William Johnson and developed significantly by E. J. Corey and Michael Chaykovsky . The reaction involves addition of a sulfur ylide to a ketone , aldehyde , imine , or enone to produce the corresponding 3 @-@ membered ring . The reaction is <unk> favoring trans substitution in the product regardless of the initial stereochemistry . The synthesis of epoxides via this method serves as an important <unk> alternative to the traditional epoxidation reactions of olefins .
|
[
383,
5030,
784,
24154,
784,
609,
323,
21862,
15688,
6317,
357,
3360,
6412,
284,
355,
262,
24154,
784,
609,
323,
21862,
15688,
6317,
393,
327,
9419,
1267,
318,
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5931,
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21263,
286,
2462,
1140,
1460,
837,
35560,
343,
312,
1127,
837,
290,
1279,
2954,
29,
764,
632,
373,
5071,
287,
20510,
416,
317,
13,
3977,
5030,
290,
4166,
5566,
416,
412,
13,
449,
13,
24154,
290,
3899,
609,
323,
21862,
15688,
764,
383,
6317,
9018,
3090,
286,
257,
37402,
331,
75,
485,
284,
257,
22354,
505,
837,
257,
35209,
39175,
837,
545,
500,
837,
393,
551,
505,
284,
4439,
262,
11188,
513,
2488,
12,
31,
1066,
9451,
5858,
764,
383,
6317,
318,
1279,
2954,
29,
43567,
1007,
32097,
287,
262,
1720,
7692,
286,
262,
4238,
10268,
37074,
764,
383,
21263,
286,
2462,
1140,
1460,
2884,
428,
2446,
9179,
355,
281,
1593,
1279,
2954,
29,
5559,
284,
262,
4569,
2462,
1140,
24765,
12737,
286,
267,
293,
69,
1040,
764,
220,
198
] |
The reaction is most often employed for epoxidation via methylene transfer , and to this end has been used in several notable total syntheses ( See Synthesis of epoxides below ) . Additionally detailed below are the history , mechanism , scope , and enantioselective variants of the reaction . Several reviews have been published .
|
[
383,
6317,
318,
749,
1690,
9322,
329,
2462,
1140,
24765,
2884,
27664,
1734,
4351,
837,
290,
284,
428,
886,
468,
587,
973,
287,
1811,
12411,
2472,
24983,
274,
357,
4091,
26375,
8497,
286,
2462,
1140,
1460,
2174,
1267,
764,
12032,
6496,
2174,
389,
262,
2106,
837,
9030,
837,
8354,
837,
290,
551,
17096,
577,
801,
425,
17670,
286,
262,
6317,
764,
12168,
8088,
423,
587,
3199,
764,
220,
198
] |
= = History = =
|
[
796,
796,
7443,
796,
796,
220,
198
] |
The original publication by Johnson concerned the reaction of 9 @-@ <unk> <unk> with substituted benzaldehyde derivatives . The attempted Wittig @-@ like reaction failed and a <unk> oxide was obtained instead , noting that " Reaction between the sulfur <unk> and <unk> did not afford <unk> as had the phosphorus and arsenic <unk> . "
|
[
383,
2656,
9207,
416,
5030,
5213,
262,
6317,
286,
860,
2488,
12,
31,
1279,
2954,
29,
1279,
2954,
29,
351,
31601,
39601,
44895,
28486,
764,
383,
7482,
38005,
328,
2488,
12,
31,
588,
6317,
4054,
290,
257,
1279,
2954,
29,
30788,
373,
6492,
2427,
837,
10820,
326,
366,
39912,
1022,
262,
37402,
1279,
2954,
29,
290,
1279,
2954,
29,
750,
407,
5368,
1279,
2954,
29,
355,
550,
262,
48980,
290,
48884,
1279,
2954,
29,
764,
366,
220,
198
] |
The subsequent development of ( <unk> ) methanide , ( CH3 ) <unk> and ( <unk> ) methanide , ( CH3 ) <unk> ( known as Corey – Chaykovsky reagents ) by Corey and Chaykovsky as efficient methylene @-@ transfer reagents established the reaction as a part of the organic canon .
|
[
383,
8840,
2478,
286,
357,
1279,
2954,
29,
1267,
1138,
7637,
485,
837,
357,
5870,
18,
1267,
1279,
2954,
29,
290,
357,
1279,
2954,
29,
1267,
1138,
7637,
485,
837,
357,
5870,
18,
1267,
1279,
2954,
29,
357,
1900,
355,
24154,
784,
609,
323,
21862,
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302,
49638,
1267,
416,
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290,
609,
323,
21862,
15688,
355,
6942,
27664,
1734,
2488,
12,
31,
4351,
302,
49638,
4920,
262,
6317,
355,
257,
636,
286,
262,
10469,
18061,
764,
220,
198
] |
= = Mechanism = =
|
[
796,
796,
13438,
1042,
796,
796,
220,
198
] |
The reaction mechanism for the Johnson – Corey – Chaykovsky reaction consists of nucleophilic addition of the ylide to the carbonyl or imine group . A negative charge is transferred to the heteroatom and because the sulfonium cation is a good leaving group it gets expelled forming the ring . In the related Wittig reaction , the formation of the much stronger phosphorus @-@ oxygen double bond prevents <unk> formation and instead , <unk> takes place through a 4 @-@ membered cyclic intermediate .
|
[
383,
6317,
9030,
329,
262,
5030,
784,
24154,
784,
609,
323,
21862,
15688,
6317,
10874,
286,
17751,
2522,
41896,
3090,
286,
262,
331,
75,
485,
284,
262,
13265,
1647,
75,
393,
545,
500,
1448,
764,
317,
4633,
3877,
318,
11172,
284,
262,
14445,
15073,
296,
290,
780,
262,
22443,
261,
1505,
269,
341,
318,
257,
922,
4305,
1448,
340,
3011,
27307,
14583,
262,
5858,
764,
554,
262,
3519,
38005,
328,
6317,
837,
262,
9978,
286,
262,
881,
7387,
48980,
2488,
12,
31,
11863,
4274,
6314,
15174,
1279,
2954,
29,
9978,
290,
2427,
837,
1279,
2954,
29,
2753,
1295,
832,
257,
604,
2488,
12,
31,
1066,
9451,
11700,
291,
19898,
764,
220,
198
] |
The trans diastereoselectivity observed results from the reversibility of the initial addition , allowing equilibration to the favored anti betaine over the syn betaine . Initial addition of the ylide results in a betaine with adjacent charges ; density functional theory calculations have shown that the rate @-@ limiting step is rotation of the central bond into the conformer necessary for backside attack on the sulfonium .
|
[
383,
1007,
2566,
459,
567,
577,
801,
3458,
6515,
2482,
422,
262,
10372,
2247,
286,
262,
4238,
3090,
837,
5086,
1602,
22282,
1358,
284,
262,
19344,
3098,
731,
5718,
625,
262,
6171,
731,
5718,
764,
20768,
3090,
286,
262,
331,
75,
485,
2482,
287,
257,
731,
5718,
351,
15909,
4530,
2162,
12109,
10345,
4583,
16765,
423,
3402,
326,
262,
2494,
2488,
12,
31,
15637,
2239,
318,
13179,
286,
262,
4318,
6314,
656,
262,
369,
16354,
3306,
329,
736,
1589,
1368,
319,
262,
22443,
261,
1505,
764,
220,
198
] |
The degree of reversibility in the initial step ( and therefore the diastereoselectivity ) depends on four factors , with greater reversibility corresponding to higher selectivity :
|
[
383,
4922,
286,
10372,
2247,
287,
262,
4238,
2239,
357,
290,
4361,
262,
2566,
459,
567,
577,
801,
3458,
1267,
8338,
319,
1440,
5087,
837,
351,
3744,
10372,
2247,
11188,
284,
2440,
2922,
3458,
1058,
220,
198
] |
Stability of the substrate with higher stability leading to greater reversibility by favoring the starting material over the betaine .
|
[
47865,
286,
262,
32305,
351,
2440,
10159,
3756,
284,
3744,
10372,
2247,
416,
43567,
262,
3599,
2587,
625,
262,
731,
5718,
764,
220,
198
] |
Stability of the ylide with higher stability similarly leading to greater reversibility .
|
[
47865,
286,
262,
331,
75,
485,
351,
2440,
10159,
12470,
3756,
284,
3744,
10372,
2247,
764,
220,
198
] |
<unk> hindrance in the betaine with greater hindrance leading to greater reversibility by <unk> formation of the intermediate and slowing the rate @-@ limiting rotation of the central bond .
|
[
1279,
2954,
29,
16222,
8132,
287,
262,
731,
5718,
351,
3744,
16222,
8132,
3756,
284,
3744,
10372,
2247,
416,
1279,
2954,
29,
9978,
286,
262,
19898,
290,
21605,
262,
2494,
2488,
12,
31,
15637,
13179,
286,
262,
4318,
6314,
764,
220,
198
] |
<unk> of charges in the betaine by <unk> such as lithium with greater solvation allowing more facile rotation in the betaine intermediate , lowering the amount of reversibility .
|
[
1279,
2954,
29,
286,
4530,
287,
262,
731,
5718,
416,
1279,
2954,
29,
884,
355,
28444,
351,
3744,
1540,
10473,
5086,
517,
1777,
576,
13179,
287,
262,
731,
5718,
19898,
837,
21683,
262,
2033,
286,
10372,
2247,
764,
220,
198
] |
= = Scope = =
|
[
796,
796,
41063,
796,
796,
220,
198
] |
The application of the Johnson – Corey – Chaykovsky reaction in organic synthesis is diverse . The reaction has come to encompass reactions of many types of sulfur ylides with electrophiles well beyond the original publications . It has seen use in a number of high @-@ profile total syntheses , as detailed below , and is generally recognized as a powerful transformative tool in the organic repertoire .
|
[
383,
3586,
286,
262,
5030,
784,
24154,
784,
609,
323,
21862,
15688,
6317,
287,
10469,
21263,
318,
10084,
764,
383,
6317,
468,
1282,
284,
44006,
12737,
286,
867,
3858,
286,
37402,
331,
75,
1460,
351,
1742,
10051,
2915,
880,
3675,
262,
2656,
16125,
764,
632,
468,
1775,
779,
287,
257,
1271,
286,
1029,
2488,
12,
31,
7034,
2472,
24983,
274,
837,
355,
6496,
2174,
837,
290,
318,
4143,
8018,
355,
257,
3665,
43590,
2891,
287,
262,
10469,
42515,
764,
220,
198
] |
= = = Types of ylides = = =
|
[
796,
796,
796,
24897,
286,
331,
75,
1460,
796,
796,
796,
220,
198
] |
Many types of ylides can be prepared with various functional groups both on the anionic carbon center and on the sulfur . The substitution pattern can influence the ease of preparation for the reagents ( typically from the sulfonium halide , e.g. <unk> iodide ) and overall reaction rate in various ways . The general format for the reagent is shown on the right .
|
[
4650,
3858,
286,
331,
75,
1460,
460,
307,
5597,
351,
2972,
10345,
2628,
1111,
319,
262,
281,
26523,
6588,
3641,
290,
319,
262,
37402,
764,
383,
32097,
3912,
460,
4588,
262,
10152,
286,
11824,
329,
262,
302,
49638,
357,
6032,
422,
262,
22443,
261,
1505,
10284,
485,
837,
304,
13,
70,
13,
1279,
2954,
29,
41080,
485,
1267,
290,
4045,
6317,
2494,
287,
2972,
2842,
764,
383,
2276,
5794,
329,
262,
302,
25781,
318,
3402,
319,
262,
826,
764,
220,
198
] |
Use of a sulfoxonium allows more facile preparation of the reagent using weaker bases as compared to sulfonium ylides . ( The difference being that a sulfoxonium contains a doubly bonded oxygen whereas the sulfonium does not . ) The former react slower due to their increased stability . In addition , the <unk> by @-@ products of sulfoxonium reagents are greatly preferred to the significantly more toxic , volatile , and odorous <unk> by @-@ products from sulfonium reagents .
|
[
5765,
286,
257,
22443,
1140,
261,
1505,
3578,
517,
1777,
576,
11824,
286,
262,
302,
25781,
1262,
17642,
12536,
355,
3688,
284,
22443,
261,
1505,
331,
75,
1460,
764,
357,
383,
3580,
852,
326,
257,
22443,
1140,
261,
1505,
4909,
257,
3385,
306,
40270,
11863,
9472,
262,
22443,
261,
1505,
857,
407,
764,
1267,
383,
1966,
6324,
13611,
2233,
284,
511,
3220,
10159,
764,
554,
3090,
837,
262,
1279,
2954,
29,
416,
2488,
12,
31,
3186,
286,
22443,
1140,
261,
1505,
302,
49638,
389,
9257,
9871,
284,
262,
5566,
517,
11422,
837,
22750,
837,
290,
16298,
9610,
1279,
2954,
29,
416,
2488,
12,
31,
3186,
422,
22443,
261,
1505,
302,
49638,
764,
220,
198
] |
The vast majority of reagents are <unk> at the ylide carbon ( either R1 or R2 as hydrogen ) . <unk> reagents are much rarer but have been described :
|
[
383,
5909,
3741,
286,
302,
49638,
389,
1279,
2954,
29,
379,
262,
331,
75,
485,
6588,
357,
2035,
371,
16,
393,
371,
17,
355,
17669,
1267,
764,
1279,
2954,
29,
302,
49638,
389,
881,
4071,
81,
475,
423,
587,
3417,
1058,
220,
198
] |
If the ylide carbon is substituted with an electron @-@ withdrawing group ( EWG ) , the reagent is referred to as a stabilized ylide . These , similarly to sulfoxonium reagents , react much slower and are typically easier to prepare . These are limited in their usefulness as the reaction can become prohibitively sluggish : examples involving amides are widespread , with many fewer involving esters and virtually no examples involving other EWG 's . For these , the related <unk> reaction is typically more appropriate .
|
[
1002,
262,
331,
75,
485,
6588,
318,
31601,
351,
281,
11538,
2488,
12,
31,
36395,
1448,
357,
43255,
38,
1267,
837,
262,
302,
25781,
318,
6412,
284,
355,
257,
44945,
331,
75,
485,
764,
2312,
837,
12470,
284,
22443,
1140,
261,
1505,
302,
49638,
837,
6324,
881,
13611,
290,
389,
6032,
4577,
284,
8335,
764,
2312,
389,
3614,
287,
511,
37496,
355,
262,
6317,
460,
1716,
6221,
1800,
306,
40186,
1058,
6096,
7411,
716,
1460,
389,
10095,
837,
351,
867,
7380,
7411,
1658,
1010,
290,
9826,
645,
6096,
7411,
584,
43255,
38,
705,
82,
764,
1114,
777,
837,
262,
3519,
1279,
2954,
29,
6317,
318,
6032,
517,
5035,
764,
220,
198
] |
If the ylide carbon is substituted with an aryl or allyl group , the reagent is referred to as a semi @-@ stabilized ylide . These have been developed extensively , second only to the classical methylene reagents ( R1 = R2 = H ) . The substitution pattern on aryl reagents can heavily influence the selectivity of the reaction as per the criteria above .
|
[
1002,
262,
331,
75,
485,
6588,
318,
31601,
351,
281,
257,
563,
75,
393,
477,
2645,
1448,
837,
262,
302,
25781,
318,
6412,
284,
355,
257,
10663,
2488,
12,
31,
44945,
331,
75,
485,
764,
2312,
423,
587,
4166,
20823,
837,
1218,
691,
284,
262,
15993,
27664,
1734,
302,
49638,
357,
371,
16,
796,
371,
17,
796,
367,
1267,
764,
383,
32097,
3912,
319,
257,
563,
75,
302,
49638,
460,
7272,
4588,
262,
2922,
3458,
286,
262,
6317,
355,
583,
262,
9987,
2029,
764,
220,
198
] |
If the ylide carbon is substituted with an alkyl group the reagent is referred to as an <unk> ylide . The size of the alkyl groups are the major factors in selectivity with these reagents .
|
[
1002,
262,
331,
75,
485,
6588,
318,
31601,
351,
281,
435,
2584,
75,
1448,
262,
302,
25781,
318,
6412,
284,
355,
281,
1279,
2954,
29,
331,
75,
485,
764,
383,
2546,
286,
262,
435,
2584,
75,
2628,
389,
262,
1688,
5087,
287,
2922,
3458,
351,
777,
302,
49638,
764,
220,
198
] |
The R @-@ groups on the sulfur , though typically <unk> , have been used to synthesize reagents that can perform enantioselective variants of the reaction ( See Variations below ) . The size of the groups can also influence diastereoselectivity in <unk> substrates .
|
[
383,
371,
2488,
12,
31,
2628,
319,
262,
37402,
837,
996,
6032,
1279,
2954,
29,
837,
423,
587,
973,
284,
24983,
1096,
302,
49638,
326,
460,
1620,
551,
17096,
577,
801,
425,
17670,
286,
262,
6317,
357,
4091,
15965,
602,
2174,
1267,
764,
383,
2546,
286,
262,
2628,
460,
635,
4588,
2566,
459,
567,
577,
801,
3458,
287,
1279,
2954,
29,
47294,
689,
764,
220,
198
] |
= = = Synthesis of epoxides = = =
|
[
796,
796,
796,
26375,
8497,
286,
2462,
1140,
1460,
796,
796,
796,
220,
198
] |
Reactions of sulfur ylides with ketones and aldehydes to form epoxides are by far the most common application of the Johnson – Corey – Chaykovsky reaction . Examples involving complex substrates and ' exotic ' ylides have been reported , as shown below .
|
[
797,
4658,
286,
37402,
331,
75,
1460,
351,
22354,
1952,
290,
257,
35209,
15511,
274,
284,
1296,
2462,
1140,
1460,
389,
416,
1290,
262,
749,
2219,
3586,
286,
262,
5030,
784,
24154,
784,
609,
323,
21862,
15688,
6317,
764,
21066,
7411,
3716,
47294,
689,
290,
705,
21036,
705,
331,
75,
1460,
423,
587,
2098,
837,
355,
3402,
2174,
764,
220,
198
] |
The reaction has been used in a number of notable total syntheses including the Danishefsky Taxol total synthesis , which produces the chemotherapeutic drug taxol , and the Kuehne <unk> total synthesis which produces the pesticide strychnine .
|
[
383,
6317,
468,
587,
973,
287,
257,
1271,
286,
12411,
2472,
24983,
274,
1390,
262,
6035,
271,
258,
9501,
2584,
9241,
349,
2472,
21263,
837,
543,
11073,
262,
4607,
847,
1758,
18089,
2563,
1687,
349,
837,
290,
262,
509,
518,
71,
710,
1279,
2954,
29,
2472,
21263,
543,
11073,
262,
36466,
336,
563,
1349,
500,
764,
220,
198
] |
= = = Synthesis of aziridines = = =
|
[
796,
796,
796,
26375,
8497,
286,
35560,
343,
312,
1127,
796,
796,
796,
220,
198
] |
The synthesis of aziridines from <unk> is another important application of the Johnson – Corey – Chaykovsky reaction and provides an alternative to amine transfer from <unk> . Though less widely applied , the reaction has a similar substrate scope and functional group tolerance to the carbonyl equivalent . The examples shown below are representative ; in the latter , an <unk> forms in situ and is opened via nucleophilic attack to form the corresponding amine .
|
[
383,
21263,
286,
35560,
343,
312,
1127,
422,
1279,
2954,
29,
318,
1194,
1593,
3586,
286,
262,
5030,
784,
24154,
784,
609,
323,
21862,
15688,
6317,
290,
3769,
281,
5559,
284,
716,
500,
4351,
422,
1279,
2954,
29,
764,
7486,
1342,
6768,
5625,
837,
262,
6317,
468,
257,
2092,
32305,
8354,
290,
10345,
1448,
15621,
284,
262,
13265,
1647,
75,
7548,
764,
383,
6096,
3402,
2174,
389,
8852,
2162,
287,
262,
6846,
837,
281,
1279,
2954,
29,
5107,
287,
34074,
290,
318,
4721,
2884,
17751,
2522,
41896,
1368,
284,
1296,
262,
11188,
716,
500,
764,
220,
198
] |
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