. beta. Effect of silicon in the synperiplanar geometry

JB Lambert, EC Chelius

Index: Lambert, Joseph B.; Chelius, Erik C. Journal of the American Chemical Society, 1990 , vol. 112, # 22 p. 8120 - 8126

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Citation Number: 81

Abstract

Abstract: The effect of silicon on the development of@ positive charge has been measured for the synperiplanar geometry of the Six-CX fragment in endo-3-(trimethylsilyl)-endo-2- norbornyl esters (3). Solvent effects were used to demonstrate that solvolysis took place by a carbocation mechanism. When the leaving group X was mesylate (3-OMS) and the solvent was 97% trifluoroethanol, the 0 effect was found to be about IO5 by comparison of the ...