Acetylene of 180°. Acetylene was discovered in 1836 by Edmund Davy, who identified it as a "new carburet of hydrogen". It was rediscovered in 1860 by French chemist Marcellin Berthelot, who coined the name "acétylène". Berthelot's empirical formula for acetylene (CH), as well as the alternative name "quadricarbure d'hydrogène" ("hydrogen quadricarbide"), were incorrect because chemists at that time used the wrong atomic mass for carbon (6 instead of 12). Berthelot was able to prepare this gas by passing vapours of organic compounds (methanol, ethanol, etc.) through a red-hot tube and collecting the effluent. He also found that acetylene was formed by
Bis(trimethylsilyl)acetylene Bis(trimethylsilyl)acetylene Bis(trimethylsilyl)acetylene (BTMSA) is an organosilicon compound with the formula C(Si(CH)). It is a colorless liquid that is soluble in organic solvents. This compound is used as a surrogate for acetylene. BTMSA is prepared by treating acetylene with butyl lithium followed by addition of chlorotrimethylsilane: BTMSA is used as a nucleophile in Friedel-Crafts type acylations and alkylations and a precursor to lithium trimethylsilylacetylide. The TMS groups can be removed with tetra-n-butylammonium fluoride (TBAF) and replaced with protons. BTMSA is also a useful reagent in cycloaddition reactions. Illustrating its versatility, BTMSA was used in a concise total synthesis of (±)-estrone. A