108893-72-7Relevant articles and documents
GRIGNARD AND HYDRIDE ADDITION TO A KETENE INTERMEDIATE: A NOVEL ACCESS TO α-DAMASCONE AND α-CYCLOCITRAL
Naef, Ferdinand,Decorzant, Rene
, p. 3245 - 3250 (2007/10/02)
α-Damascone (1), a rose fragrance chemical, was synthesized by an allylmagnesium chloride addition to ketene 7 as key step.When the same ketene 7 was reduced by two different aluminium hydride reagents, α-cyclocitral was obtained.The presumed intermediates, enolates II and III, were first trapped as silyl enol ethers and then hydrolyzed with D2O to give the expected α-monodeuterated carbonyl compounds.Mixed aluminium hydride reduction of ketenes is recommended as a facile entry into the chemistry of aldehyde enolates.