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Reactions with Phosphinealkylenes, XXXIX. - New Methods for the Preparation of 1-Bromoacetylenes and Enynes
Bestmann, Hans Juergen,Frey, Herbert
, p. 2061 - 2071 (2007/10/02)
1,1-Dibromoolefins 4 are obtained in good yield from the reaction of aldehydes 1 with triphenylphosphane (2) and carbon tetrabromide (3).Reaction of 4 with three moles of methylene(triphenyl)phosphorane (8) leads to the propargylidene(triphenyl)phosphoranes 11 which react with aldehydes to give the enynes 13.The ylides 11 can also prepared via the reaction of bromoacetylenes 7, which can be obtained from 4, with two moles of 8.This reaction sequence allows the synthesis of new retinoids with enyne structures from retinal.
