Canadian Journal of Chemistry

Open chain nitrogen compounds. Part X. Thermolysis of α-diazoacetanilides in methanol: a convenient synthesis of α-methoxyacetanilides from ethyl N-(arylazo) …

KUKG Nicholas, K Vaughan

Index: Nicholas, Kumudini U. K. Gamage; Vaughan, Keith Canadian Journal of Chemistry, 1986 , vol. 64, p. 799 - 802

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Abstract

α-Diazoacetanilides (4), which are readily available from the open-chain triazenes (2), undergo thermolysis in methanol solution to afford the α-methoxyacetanilides (5), an apparently rare type of ether/amide derivative. The methanolic thermolysis is inhibited by the presence of a tertiary amine in the solvent, suggesting that a carbocation, rather than a carbene, intermediate is involved in the conversion of the diazo-amide to the methyl ether. ...