N-Fluorobis [(perfluoroalkyl) sulfonyl] imides: reactions with some olefins via. alpha.-fluoro carbocationic intermediates

DD DesMarteau, ZQ Xu, M Witz

Index: DesMarteau, Darryl D.; Xu, Ze-Qi; Witz, Michael Journal of Organic Chemistry, 1992 , vol. 57, # 2 p. 629 - 635

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Citation Number: 93

Abstract

Summary The solvolysis reaction of 1-Br proceeds through the highly unstable carbocation intermediate 2, which has an estimated half-life in water of ca. 30 ns. In spite of the high reactivity of 2, the ion-pair intermediate [2. Br-] of the reaction of 1-Br escapes to form free ions before there is a signifcant reaction of solvent (kd> 3OOk,', Scheme III). The Winstein model for solvolysis reactions includes three types of carbocation intermediates, each of ...