In 1960, Vogel discovered that 1,2-divinylcyclopropane rearranges to cycloheptan-1,4-diene., After his discovery, a series of intense mechanistic investigations of the reaction followed in the 1960s, as researchers realized it bore resemblance (both structural and mechanistic) to the related rearrangement of vinylcyclopropane to cyclopentene. By the 1970s, the rearrangement had achieved synthetic utility and to this day it continues to be a useful method for the formation of seven-membered rings. Variations incorporating heteroatoms have been reported (see below).
Advantages: Being a rearrangement, the process exhibits ideal atom economy. It often proceeds spontaneously without the need for a catalyst. Competitive pathways are minimal for the all-carbon rearrangement.
Disadvantages: The configuration of the starting materials needs be controlled in many cases—trans-divinylcyclopropanes often require heating to facilitate isomerization before rearrangement will occur. Rearrangements involving heteroatoms can exhibit reduced yields due to the formation of side products.