Reactions of alpha,beta-enones with diazo compounds part 3 on the nature of the 1,5-ring closure of alpha,beta-enone ylides


Anac O., Ozdemir A., SEZER Ö.

HELVETICA CHIMICA ACTA, vol.86, no.2, pp.290-298, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 86 Issue: 2
  • Publication Date: 2003
  • Doi Number: 10.1002/hlca.200390030
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.290-298
  • Istanbul Technical University Affiliated: No

Abstract

Carbonyl ylides arising from ethyl acetodiazoacetate/dimethyl diazomalonate and a,beta-enones with mainly s-cis conformations underwent disrotatory cyclization to produce dihydrofuran derivatives. This process proved to be sensitive to steric effects. The corresponding ylides arising from rather s-trans a,beta-enals yielded dioxole derivatives. The mechanisms of the reactions are discussed.