4,5-DIMETHYLENE-1,2-DIOXANE AND DERIVED DIELS-ALDER ADDUCTS


ATASOY B., KARABOCEK S.

TETRAHEDRON LETTERS, vol.33, no.52, pp.8127-8130, 1992 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 33 Issue: 52
  • Publication Date: 1992
  • Doi Number: 10.1016/s0040-4039(00)74738-1
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.8127-8130
  • Gazi University Affiliated: No

Abstract

4,5-Dimethylene-1,2-dioxane (1) was prepared by zinc-induced debromination of 4.5-bis (bromomethyl)-1,2-dioxacylohexa-4-en (4) obtained from 2,3-bis (bromomethly-1,3-butadiene (3) by reaction with singlet oxygen. Diels-Alder additions of 1 with singlet oxygen, dimethyl acetylenedicarboxylate and N-methyl-1,2,4-triazoline-3,5-dione gave adducts 2,6 and 8 respectively. 3,4-Disubtituted furans 5 and 9 were obtained from peroxides 4 and 8 by cobalt (II) tetraphenylporphyrin catalyzed rearrangement.