Acetoxylation by aryliodoso acetates. III. Effects of structural changes in the reactants

Abstract

Definite increases in rate of reaction between aryliodoso acetates and N-arylacetamides occur when electron-releasing groups are introduced into the N-arylacetamide nucleus, the Arrhenius A and E parameters decreasing simultaneously; electron-attracting substituents cause the reverse effects. Small, erratic changes in rate and the Arrhenius parameters accompany substitution in the aryliodoso nucleus. N-Methylation of aceto-p-toluidide inhibits the reaction completely. Possible mechanisms are briefly discussed.