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

B Atasoy, R Özen

Index: Atasoy, Basri; Oezen, Recep Tetrahedron, 1997 , vol. 53, # 40 p. 13867 - 13872

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Citation Number: 11

Abstract

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- ...