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 (CH 2 NH, H 2 CO, N 2, CO, and HCN from N 3 CH 2 CH 2 OH and C 2 H 4, CH 2 NH, HCN, CO 2, and N 2 from N 3 CH 2 COOCH 2 CH 3 ) 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.
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Hooper et al. (2002) studied this question.
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