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Synthesis and Reactivity of Carbohydroximoyl Azides: I. Aliphatic and Aromatic Carbohydroximoyl Azides and 5-Substituted 1-Hydroxytetrazoles Based Thereon

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Abstract

Chlorination of 1-hydroxyiminopentane gave 1-chloro-1-nitrosopentane which reacted with sodium azide in DMF to form pentanohydroximoyl azide. The azidation of benzohydroximoyl chlorides was always accompanied by decomposition to benzonitriles. Treatment of carbohydroximoyl azides in ether with gaseous hydrogen chloride afforded 5-butyl- and 5-aryl-1-hydroxytetrazoles which reacted with acetic anhydride to form the corresponding acetates.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 198013, Russia

    I. V. Tselinskii, S. F. Mel'nikova & T. V. Romanova

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  1. I. V. Tselinskii
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  2. S. F. Mel'nikova
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  3. T. V. Romanova
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Tselinskii, I.V., Mel'nikova, S.F. & Romanova, T.V. Synthesis and Reactivity of Carbohydroximoyl Azides: I. Aliphatic and Aromatic Carbohydroximoyl Azides and 5-Substituted 1-Hydroxytetrazoles Based Thereon. Russian Journal of Organic Chemistry 37, 430–436 (2001). https://doi.org/10.1023/A:1012453012799

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  • DOI: https://doi.org/10.1023/A:1012453012799

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