The Journal of Organic Chemistry

Photochemical Beckmann rearrangements. Correspondence between substituent effects in oximes and oxaziridines

Y Ogata, K Takagi, K Mizuno

Index: Ogata, Yoshiro; Tagaki, Katsuhiko; Mizuno, Kiyohiko Journal of Organic Chemistry, 1982 , vol. 47, p. 3684 - 3687

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Citation Number: 18

Abstract

he relative migratory tendencies of hydrogen and aryl groups in the photochemical Beckmann rearrangement of benzaldoximes 2a-c were compared with those in the photochemical rearrangement of 2-aky1-3-aryloxaziridines 3a-f. The migratory tendencies depended on the nature of the aryl substituent and were similar in 2a-c and 3a-q implying that the photochemical Beckmann rearrangement proceeds through an oxaziridine ...