The Journal of Organic Chemistry

Generation of benzyne in the thermal decomposition of 2-carboxyphenyl p-toluenesulfonate

SV Luis, P Ferrer, MI Burguete

Index: Luis, Santiago V.; Ferrer, Patrick; Burguete, M. Isabel Journal of Organic Chemistry, 1990 , vol. 55, # 12 p. 3808 - 3812

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Citation Number: 5

Abstract

The scope and the mechanism of the generation of 1, 2-dehydrobenzene in the thermal decomposition of 2-carboxyphenyl p-toluenesulfonate and its salts (3) have been studied. 1, 2-Dehydrobenzene, which can be trapped with dienic or nucleophilic reagents, is formed in a nonconcerted process with the intermediacy of a species C6H4C02 (1 I)(probably benzoxet-2-one). A complex mixture of disalicylide, trisalicylide, and some other ...