Synthesis of 3,4-disubstituted furans via unsaturated cyclic peroxides arising by photooxygenation of 2,3-bis (bromomethyl)-1,3-butadiene and derived exocyclic dienes

Atasoy B., Ozen R.

TETRAHEDRON, cilt.53, sa.40, ss.13867-13872, 1997 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 53 Konu: 40
  • Basım Tarihi: 1997
  • Doi Numarası: 10.1016/s0040-4020(97)00875-2
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayıları: ss.13867-13872


The reaction of 2,3-bis (bromomethyl)-1,3-butadiene (3) with singlet oxygen resulted in the formation of a peroxide (4) which rearanged with CoTPP to bis(bromomethyl)furan. Zinc-induced debromination of cycloadducts which were obtained from the [2+4] Diels-Alder reactions of 3 with DMAD and benzyne gave exocyclic dienes 7 and 11 from which fused ring furans were prepared by photooxygenation followed by rearrangement. 4,5-Dimethylene-1,2-dioxane (14) was synthesized by zinc-induced debromination of 4. The cycloaddition reactions of 14 with MTAD, singlet oxygen and DMAD were studied. (C) 1997 Elsevier Science Ltd.