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

M Ochiai, T Ukita, S Iwaki, Y Nagao…

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

Full Text: HTML

Citation Number: 29

Abstract

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 ( ...