The Journal of Organic Chemistry

o-Benzoquinone methide: an intermediate in the gas-phase pyrolysis of chroman

GC Paul, JJ Gajewski

Index: Paul, Gitendra C.; Gajewski, Joseph J. Journal of Organic Chemistry, 1993 , vol. 58, # 19 p. 5060 - 5062

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Citation Number: 22

Abstract

Gas-phase pyrolysis of chroman gives o-cresol, benzofuran, and styrene in a 4: 2: 1 ratio at 413" C. In the presence of 2-butene, a moderately stereospecific 4+ 2 reaction occurs with the likely intermediate, o-benzoquinone methide, 1. The addition of 2-butene increased the amount of reaction and decreased the extent of formation of benzofuran and styrene. Addition of hydrogen gas increased the amount of hydrodealkoxylation product, styrene, ...

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