. gamma.-Silicon stabilization of carbonium ions in solvolysis. 2. Solvolysis of 4-(trimethylsilyl)-2-butyl p-bromobenzenesulfonates

VJ Shiner Jr, MW Ensinger…

Index: Shiner, V. J.; Ensinger, Mark W.; Rutkowske, Randy D. Journal of the American Chemical Society, 1987 , vol. 109, # 3 p. 804 - 809

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Citation Number: 42

Abstract

Abstract: The solvolysis of 4-(trimethylsilyl)-2-butyl p-bromobenzenesulfonate produces racemic substitution products and a minor amount of methylcyclopropane at a rate which is several-fold faster than the solvolysis of its carbon analogue; polarimetric and conductometric rates are not significantly different. Added LiC104, KOH, KOBs, and LiOBs produced normal salt effects on the polarimetric rate; b values varied from 0.2 to 130, ...