The. GAMMA.-Silicon Effect. IV. The Solvolysis Mechanism of 3-(Aryldimethylsilyl) propyl p-Toluenesulfonates.

T Nakashima, R Fujiyama, HJ Kim, M Fujio…

Index: Fujiyama; Nakashima; Kim; Fujio; Tsuno Bulletin of the Chemical Society of Japan, 2000 , vol. 73, # 2 p. 429 - 438

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Citation Number: 11

Abstract

Solvolysis rates of 3-(aryldimethylsilyl) propyl p-toluenesulfonates were determined in various solvents. The reaction mechanism of this simple γ-silyl system was clarified based on the solvent effect and the substituent effect analyses. The solvent effect on this system clearly showed the nucleophilic assistance of solvent, but failed to correlate linearly with the extended Winstein-Grunwald equation, substantiating that the reaction should not ...