Reactions of Aryl Diazonium Salts and Arylazo Alkyl Ethers. IV. Substituent Effects on the Rates of Some Reactions of syn-Arylazo Ethyl Ethers in Ethanol

Abstract

Substituent effects on the rates of ionization (k_IS), decomposition (k_D) and syn-anti interconversion (k_p) for a number of syn-arylazo ethyl ethers have been measured. The rates of ionization and syn-anti interconversion correlate well with sigma while the rates of decomposition correlate with σ⁺. Substituent effects on the ionization of the syn-ethers are compared to those for ionization of the anti-ethers. Substituent effects on the rate of syn-anti interconversion support the proposed ionization-recombination mechanism.