Photochemical rearrangements of 1, 2-benzisoxazolinones

TH Kinstle, LJ Darlage, CL McIntosh

Index: Darlage,L.J. et al. Journal of Organic Chemistry, 1971 , vol. 36, p. 1088 - 1093

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Citation Number: 17

Abstract

Irradiation of 3-hydroxy-l, 2-benzisoxazole (3) results in the formation of benaoxazolinone (4). This photoisomerization is shown to occur predominantly via the keto tautomer 3b since facile rearrangements of the N-alkyl-l, 2-beneisoxazolinones (19) occur under similar photolytic conditions. A mechanism involving a diradical species is proposed for this reaction. Low temperature photolysis-infrared measurements support this mechanism ...