The Journal of organic chemistry

Remarkably facile solvolyses of triflates via carbocationic processes in dimethyl sulfoxide

X Creary, EA Burtch

Index: Creary, Xavier; Burtch, Elizabeth A. Journal of Organic Chemistry, 2004 , vol. 69, # 4 p. 1227 - 1234

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Citation Number: 11

Abstract

A number of triflates have been shown to undergo clean pseudo-first-order solvolysis reactions in DMSO-d 6 to give products derived from carbocationic intermediates. Thus, t- BuCH (OTf) CO-t-Bu (5) and t-BuCH2OTf (9) react readily in DMSO-d 6 at 25° C to give a rearranged oxosulfonium salts, and subsequent alkene products where methyl migration to the incipient cationic center occurs. t-BuCH (OTf) CO2CH3 (14) gives analogous ...