Kinetics and mechanism of the decomposition of 3-alkyl-1-aryltriazenes by carboxylic acids

Abstract

A kinetic study of reactions between a series of 3-alkyl-1-aryltriazenes with benzoic acids to yield alkyl benzoates supports a mechanism in which proton transfer and departure of an alkyl cation are rate-determining and synchronous. The resulting alkyl cation–carboxylate ion-pair may suffer nucleophilic attack or Wagner–Meerwein rearrangement before collapsing to product.