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Kinetics and mechanism of base-catalyzed cleavage of some bicyclo[4.2.0.]octa-1,3,5-trien-7-one (benzocyclobuten-1(2H)-one) derivatives

✍ Scribed by Mary A. Sorial; George M. Iskander; R. Bolton

Publisher: John Wiley and Sons
Year: 1982
Tongue: English
Weight: 376 KB
Volume: 14
Category: Article
ISSN: 0538-8066
DOI: 10.1002/kin.550140808

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✦ Synopsis

Abstract

The kinetics of cleavage of 3‐hydroxybicyclo[4.2.0]octa‐1,3,5‐trien‐7‐ones in aqueous sodium hydroxide, and of the alkoxy and acetoxy analogues in methanolic sodium methoxide solution, were examined under pseudo‐first‐order reaction conditions. The dependence of the rate upon the basicity of the solvent, whether measured by H~−~ or by [OR^−^], reflects the possible structure of the transition state. The deduced mechanism is also supported by the effects of substituents upon the reaction rate. The relative amounts of the volatile reaction products derived from o‐toluic acid and from phenylacetic acid are understood in terms of the substituent effect upon the relative stabilities of the carbanions.

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