Phosphine-and phosphite-mediated difluorocarbene exchange reactions of (bromodifluoromethyl) phosphonium salts. Evidence for facile dissociation of ( …

DJ Burton, DG Naae, RM Flynn, BE Smart…

Index: Burton, Donald J.; Naae, Douglas, G.; Flynn, Richard M.; Smart, Bruce E.; Brittelli, David R. Journal of Organic Chemistry, 1983 , vol. 48, # 20 p. 3616 - 3618

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Citation Number: 26

Abstract

A 1-7 x= o ture) from 9, reacts with the sodium salt of methyl (di-methy1pho~ phinyl) bromoacetate~ in l, 2-dimethoxyethane to afford 11. Treatment of 11 with m- chloroperoxybenzoic acid gives rise to 12 as a 2: 3 mixture of E and 2 isomers. Reaction of silyl enol ether 13 (3.5 equiv) at-78" C in 1, 2-dimethoxyethane with methyllithium (2.5 equiv) generates, presumably, enolate 14, which reacts with the esters 12 (-78" C (30 min)-room ...