The mechanism of rearrangement of chorismic acid and related compounds

JJ Gajewski, J Jurayj, DR Kimbrough…

Index: Gajewski,J.J.; Jurayj,J.; Kimbrough,D.R. Journal of the American Chemical Society, 1987 , vol. 109, p. 1170

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Citation Number: 183

Abstract

Abstract: The thermal reactions of the biochemically important molecule chorismic acid are studied in solution. It undergoes two competitive reactions, one is an unusually facile Claisen rearrangement, and the other an elimination to give p-hydroxybenzoic acid and pyruvic acid. Attempts are made to understand the factors responsible for the facility of the Claisen rearrangement by preparation of a variety of analogues of chorismate. ...

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