Acid-catalyzed rearrangement of K-region arene oxides: observation of ketone intermediates and a sterically induced change in rate-determining step

NT Nashed, JM Sayer, DM Jerina

Index: Nashed, Nashaat T.; Sayer, Jane M.; Jerina, Donald M. Journal of the American Chemical Society, 1993 , vol. 115, # 5 p. 1723 - 1730

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Citation Number: 13

Abstract

Abstract: K-region arene oxides rearrange to phenols in acetonitrile in two acid-catalyzed steps: rapid rearrangement of the arene oxide to positionally isomeric keto tautomers of K- region phenols, followed by slow enolization. Accumulation of the ketones, proposed intermediates in the acid-catalyzed solvolyses of arene oxides in aqueous solution, allowed their direct spectroscopic observation and characterization for the first time under ...