Kinetic evidence for the intermediacy of 1-azirines in the gas-phase thermal isomerization of 3H-isoxazoles to. alpha.-carbonylacetonitrile derivatives

JD Perez, GI Yranzo, DA Wunderlin

Index: Perez, Jorge D.; Yranzo, Gloria I.; Wunderlin, Daniel A. Journal of Organic Chemistry, 1982 , vol. 47, # 6 p. 982 - 984

Full Text: HTML

Citation Number: 22

Abstract

Discussion The isomerization of 1 and 2 to the a-carbonylacetonitrile derivatives agrees with the results obtained in the thermal decomposition of terminal vinyl azides, which often give nitriles as the major product. It has been strongly suggested that a vinyl nitrene is a common intermediate in these reaction^.^ However, it has been shown that the photolysis of@-styryl azides6 at-30" C gives 3-phenyl-1-azirines, Pyrolysis of either this azirine or the 0-styryl ...