The Journal of Organic Chemistry

Mechanistic studies on the photochemical reactions of isoxazoles

JP Ferris, RW Trimmer

Index: Ferris,J.P.; Trimmer,R.W. Journal of Organic Chemistry, 1976 , vol. 41, p. 13 - 19

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Citation Number: 29

Abstract

The mechanisms of the photochemical conversion of isoxazoles to oxazoles and ketoketenimines have been investigated. Isonitrile 14 was detected by an ir band at 2160 cm- l in the photoconversion of 5 to 15 at-77'. Compound 14 was further identified by independent synthesis and by hydrolysis to formamide 17 in acid. Ir bands at 1690 and 1655 cm-l are consistent with the hypothesis that azirine 13 is the precursor to isonitrile 14. It is ...