Reactions of aryldiazonium salts and alkyl arylazo ethers. VIII. General acid catalysis of the ionization of alkyl (E)-arylazo ethers in alcoholic solvents

Abstract

Further studies of the general acid-catalysed ionization of alkyl (E)-arylazo ethers in alcoholic solvents have been carried out. The magnitude of catalysis and the degree of proton transfer as a function of the substituent on the aromatic ring, the alkoxide ion nucleofuge, the solvent and the ionic strength have been studied. The results are consistent with a mechanism for the acid-catalysed ionization of alkyl (E)-arylazo ethers in which proton transfer and N-O bond breaking are concerted.

¹H and ¹³C n.m.r. data for a number of alkyl p-nitrophenylazo ethers are reported.