The Journal of Organic Chemistry

Preparation of epoxides by oxidative decarboxylation of. beta.-hydroxy acids. Stereo-and regiochemistry of oxidative elimination of secondary radicals with cupric …

BB Snider, T Kwon

文献索引：Snider, Barry B.; Kwon, Taesoo Journal of Organic Chemistry, 1990 , vol. 55, # 6 p. 1965 - 1968

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被引用次数: 27

摘要

During our studies of manganese (II1)-based oxidative free-radical cyclizationsl-10 we observed to our surprise that the@-hydroxy radical 2, prepared by oxidation of the@-keto ester 1 with manganese triacetate in acetic acid, was oxidized by manganese (II1) to epoxide 3 in 3040% yield. 7 There are isolated reports that transition-metal oxidants will convert@-hydroxy radicals to epoxides. Copper (I1) has been shown to oxidize@-hydroxy ...