Doering-LaFlamme Allene Synthesis

W. von E. Doering, P. M. LaFlamme, Tetrahedron 2, 75 (1958); US 2933544 (1960).

Treatment of an olefin with bromoform and an alkoxide to yield the 1,1-dibromocyclopropane which reacts with an active metal to produce an allene:

Reviews: M. Murray, Houben-Weyl 5/2a, 985 (1977); V. Nair, Comp. Org. Syn. 4, 1009-1012 (1991).