Oxidative Grob fragmentation of. gamma.-tributylstannyl alcohols with a combination of iodosylbenzene, dicyclohexylcarbodiimide, and boron trifluoride

M Ochiai, T Ukita, S Iwaki, Y Nagao…

文献索引：Ochiai, Masahito; Ukita, Tatsuzo; Iwaki, Shigeru; Nagao, Yoshimitsu; Fujita, Eiichi Journal of Organic Chemistry, 1989 , vol. 54, # 20 p. 4832 - 4840

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被引用次数: 29

摘要

Exposure of cyclic y-stannyl alcohols, prepared from cyclic vinyl ketones, to a combination of iodosylbenzene, dicyclohexylcarbodiimide, and boron trifluoride-diethyl ether in dichloromethane undergoes an oxidative Grob fragmentation to give unsaturated carbonyl compounds. The dicyclohexylcarbodiimide in this reaction apparently activates iodosylbenzene and decreases Lewis acidity of boron trifluoride. The fact that the iodine ( ...