A Study of the Thermal Decomposition of 2-Azidoethanol and 2-Azidoethyl Acetate by Ultraviolet Photoelectron Spectroscopy and Matrix Isolation Infrared Spectroscopy

Abstract

The thermal decompositions of 2-azidoethanol and 2-azidoethyl acetate have been studied by matrix isolation infrared spectroscopy and real-time ultraviolet photoelectron spectroscopy. The products that were detected in a flow system at different temperatures (CH2NH, H2CO, N2, CO, and HCN from N3CH2CH2OH and C2H4, CH2NH, HCN, CO2, and N2 from N3CH2COOCH2CH3) allowed mechanisms for decomposition to be proposed. The experimental evidence obtained is consistent with 2-azidoethyl actetate decomposing via a concerted mechanism, similar to that found previously for azidoacetic acid, whereas the 2-azidoethanol decomposition is consistent with a stepwise decomposition mechanism as observed previously for azidoacetone.