The Journal of Organic Chemistry

The unusually slow hydrolysis rate of silyl methyl ketals in benzoquinone systems. The question of siloxy stabilization of an adjacent positive charge and …

AJ Stern, JS Swenton

Index: Stern, Alan J.; Swenton, John S. Journal of Organic Chemistry, 1989 ,  vol. 54,  # 12  p. 2953 - 2958

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Citation Number: 23

Abstract

The kinetics of the acid-catalyzed monohydrolysis of six quinone bisketals were studied under pseudefmt-order conditions. The tert-butyldimethylsilyl methyl and the tert- butyldiphenylsilyl methyl ketals respectively hydrolyze about 400 times slower than does the corresponding dimethyl ketal and react nearly at the rate of the ethylene glycol ketal. An important consideration in understanding these results was the carbonium ion stabilizing ...