作者:J.C. Pommelet、N. Manisse、J. Chuche
DOI:10.1016/s0040-4020(01)93839-6
日期:1972.1
The stereospecific synthesis of cis and trans diethylenic epoxides 5a-c is reported. Thermal rearrangement of cis epoxides gives 4,5-dihydro-oxepines 6a-c (3,3 sigmatropic reaction with boat transition state); the pyrolysis of the trans epoxides produces also 2,3-dihydro-furans 7a-c; the disrotatory ring closure of a carbonyl ylide is proposed to explain the stereospecific formation of dihydrofuranic
报道了顺式和反式二乙烯环氧化物5a-c的立体有择合成。顺式环氧化物的热重排得到4,5-二氢-氧杂环丁烷6a-c(3,3σ反应,舟皿过渡态);反式环氧化物的热解也产生2,3-二氢呋喃7a-c。为了解释二氢呋喃化合物的立体定向形成,提出了羰基内酯的可旋转的闭环。