Oxidation of alcohols with dimethyl selenide-N-chlorosuccinimide complex

K Takaki, M Yasumura, K Negoro

Index: Takaki, Ken; Yasumura, Masateru; Negoro, Kenji Journal of Organic Chemistry, 1983 , vol. 48, # 1 p. 54 - 57

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Citation Number: 15

Abstract

Scheme IV selenide 9 by treatment with NCS in 81% yield (eq 2). In contrast, y-hydroxy selenide 10 (a mixture of threo and erythro, 1: 2) was exclusively deselenized to give allylic alcohol 11 (cis/trans, 3: 7) and diphenyl diselenide in 97% and 40% yields, respectively, under similar conditions. When this reaction was carried out for a longer time, the yield of 11 was gradually decreased (-75%), and formation of enone 12 (-15%) and diene 13 (-5%) ...