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, cilt.86, ss.290-298, 2003 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 86 Konu: 2
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1002/hlca.200390030
  • Dergi Adı: HELVETICA CHIMICA ACTA
  • Sayfa Sayıları: ss.290-298

Özet

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.