131794-49-5Relevant articles and documents
Nazarov Reaction of Trisubstituted Dienones: Mechanism Involving Wagner-Meerwein Shift
Motoyoshiya, Jiro,Yazaki, Toshikazu,Hayashi, Sadao
, p. 735 - 740 (2007/10/02)
The Nazarov reactions of trisubstituted α,α'-dienones were studied.Whereas α,β-dimethyl-β'-alkyl α,α'-dienones gave 2,3-dimethyl-4-alkyl-2-cyclopentenones when heated in concentrated sulfuric acid, the reaction of β,β-dimethyl-β'-alkyl α,α'-dienones afforded 3,4-dimethyl-4-alkyl-2-cyclopentenones as the rearranged products.A mechanistic investigation using two deuterated dienones suggests that the Nazarov reactions of the latter dienones are accompanied by Wagner-Meerwein shifts to form the most stable carbocations.
