The Journal of Organic Chemistry

Steric and inductive effects on the hydrolysis of quinone bisketals

CP Chen, JS Swenton

Index: Chen, Chung-Pin; Swenton, John S. Journal of Organic Chemistry, 1985 , vol. 50, # 23 p. 4569 - 4576

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Citation Number: 11

Abstract

A second series of compounds employed in the study were designed to assess the importance of steric effects on the bisketal hydrolysis. These systems were prepared by addition of organolithium reagents or Grignard reagents to the ketone 9 followed by triethylsilane reduction. Not surprisingly, enolization was a major complication in the reaction of 9 with isopropyl and tert-butyl organometallic derivatives. This synthetic work ...