Journal of Organic Chemistry p. 982 - 984 (1982)
Update date:2022-08-11
Topics:
Perez, Jorge D.
Yranzo, Gloria I.
Wunderlin, Daniel A.
Thermal isomerization of 5-methylisoxazole and 5-amino-4-methylisoxazole to acetylacetonitrile and 2-cyanopropionamide, respectively, was studied in a flow system.The activation parameters are reported.According to the experimental results, a concerted 1,3 sigmatropic shift to 1-azirines is proposed as the rate-limiting step in these reactions.A general reaction mechanism for the isomerization of isoxazoles into 1-azirines, oxazoles, and α-carbonylacetonitrile derivatives is discussed.
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(1982)