Extremely facile ligand-exchange and disproportionation reactions of diaryl sulfoxides, selenoxides, and triarylphosphine oxides with organolithium and Grignard …

N Furukawa, S Ogawa, K Matsumura…

Index: Furukawa, Naomichi; Ogawa, Satoshi; Matsumura, Kazunori; Fujihara, Hisashi Journal of Organic Chemistry, 1991 , vol. 56, # 22 p. 6341 - 6348

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Citation Number: 68

Abstract

Diaryl sulfoxides undergo unusually rapid ligand-exchange reaction upon treatment with organolithium reagents at-95 OC. Optically pure phenyl p-tolyl sulfoxide (4b) reacted with organolithium reagents at the range from-20 to-95" C to give facile ligand-exchange and disproportionation products, ie, diphenyl sulfoxide (7), recovered 4b, and di-ptolyl sulfoxide (8) in a statistical ratio of 1: 21 in quantitative yields, and the recovered 4b wm completely ...