Electrophilic Substitution by Hydrogen in the Xylenes. The Kinetics of Acid Cleavage of the Trimethylsilylxylenes

RA Benkesser, HR Krysiak

Index: Benkeser; Krysiak Journal of the American Chemical Society, 1954 , vol. 76, p. 6353,6355,6357

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Citation Number: 22

Abstract

Pseudo first-order rate constants for the cleavage of the six isomeric trimethylsilylxylenes by fi-toluenesulfonic acid in acetic acid have been determined at 25'. Although the cleavage reactions parallel usual electrophilic substitutions, they are considerably influenced by buttressing and steric strain effects. The order of increase in the rate of acid cleavage for the trimethylsilylxylenes is (R= trimethylsilyl): 5-Rm-xylene< 4-Ro-xylene< 2-Rp-xylene< 3-Ro ...