Nazarov reaction of trisubstituted dienones: mechanism involving Wagner-Meerwein shift

J Motoyoshiya, T Yazaki, S Hayashi

文献索引：Motoyoshiya, Jiro; Yazaki, Toshikazu; Hayashi, Sadao Journal of Organic Chemistry, 1991 , vol. 56, # 18 p. 735 - 740

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被引用次数: 28

摘要

The Nazarov reactions of trisubstituted cu, cu'-dienones were studied. Whereas a&dimethyl+'-alkyl a, a'-dienones gave 2, 3-dimethyl-4-alkyl-2-cyclopentenones when heated in concentrated sulfuric acid, the reaction of O, &dimethyl-@'-alkyl cu, cu'-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 ...