The Reactions of a-Ylidene (Vinylidene, Benzylidene, Styrylmethylidene) Bis[carbonyls] with Copper Mono/Bis[carbonylcarbenoids]


Merey G. , KAYA M., Anac O.

HELVETICA CHIMICA ACTA, vol.95, no.8, pp.1409-1424, 2012 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 95 Issue: 8
  • Publication Date: 2012
  • Doi Number: 10.1002/hlca.201200004
  • Title of Journal : HELVETICA CHIMICA ACTA
  • Page Numbers: pp.1409-1424

Abstract

The [Cu(acac)2]-catalyzed reactions of various alpha,beta,gamma,delta-unsaturated bis-ketones/bis-esters/bis-keto esters with dimethyl diazomalonate and ethyl diazoacetate were studied. Total steric/electronic convenience of the present reaction paths was investigated. Methoxy/nitro substituents in m-/p-positions on benzylidene biscarbonyls did not alter the general routes of the reactions, supporting concerted mechanism. Dihydrobenzoxepine/oxepine formation was sterically sensitive to the related pre-ring conformation, and dihydrofurans were effected by both charge control and steric factors.