Canadian journal of chemistry

Mechanistic aspects of the methoxide-catalyzed transformation of 4-acyloxy-1, 3, 4-oxadiazines to N-amino-oxazolidonylhydrazones

D Mackay, DD McIntyre

Index: Mackay, Donald; McIntyre, Deane Douglas Canadian Journal of Chemistry, 1984 , vol. 62, p. 355 - 360

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Citation Number: 8

Abstract

When the 1, 3, 4-oxadiazine 2, one of three known isomers formed by cycloaddition of 2, 5- dimethyl-3, 4-diphenyl-cyclopentadienone and dimethyl azodicarboxylate, is isomerized by MeO--MeOH to the hydrazone 4, the MeO of the ester group of 2 is lost and MeO is incorporated into 4 from the solvent. In acid, eg trifluoroacetic acid, demethylation of 2 gives 14 in which the ester Me is lost. The hydrazone 4 also gives 14 with acid, but by a different ...