Triazines and related products. Part IV. Methylation of 3-aryl-3,4-di-hydro-4-immo-1,2,3-benzotriazines

H N E Stevens, M F G Stevens

Research output: Contribution to journalArticle

Abstract

The title compounds undergo ring-opening in sodium ethoxide solution and subsequent treatment with methyl iodide affords mixtures of isomeric methylated o-cyanophenyltriazenes. The structures of the products have been elucidated by reduction to the component amines with stannous chloride in hydrochloric acid, and the applicability of this reagent in the study of other o- cyanophenyltriazenes has been explored. Catalytic hydrogenation of o-nitro-phenyltriazenes yields benzotriazole as one of the products. Mechanisms for the ring-opening and reduction reactions have been proposed.

Original languageEnglish
Pages (from-to)2284-2289
Number of pages6
JournalJournal of the Chemical Society C: Organic
Issue number17
Publication statusPublished - 1970

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