Mechanisms of nucleophilic attack at carbon-nitrogen double bonds. The reaction of aryl N-arylbenzimidates with methoxide ion

Abstract

Rate data for the reaction of three series of aryl N-arylbenzimidates with methoxide ion at 303 K are presented. Linear Hammett plots were obtained for each series. Solvent isotope effects have also been measured. The results are interpreted in terms of rate-determining formation of a tetrahedral intermediate, irrespective of the nature of the substituent.