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von Braun-Rudolf Synthesis

(von Braun-Rudolf Reaction, von Braun-Rudolf Tetrazole Synthesis)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr649

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. von Braun-Rudolf Synthesis. Comprehensive Organic Name Reactions and Reagents. 649:2904–2907.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The preparation of substituted tetrazoles by the treatment of imidyl chlorides with anhydrous hydrazoic acid in benzene or chloroform, is generally known as the von Braun-Rudolf reaction, von Braun-Rudolf synthesis, or von Braun–Rudolf tetrazole synthesis. All the mechanistic features of the reaction have been discussed. It has been reported that the von Braun-Rudolf synthesis also promotes some side reactions that lead to ureas (via carbodiimides) and anilinotetrazoles under a strongly proton-donating environment. In addition, an intramolecular cyclization of azide and nitrile has been developed to form a tetrazole [5,1-c]-[1,4] benzothiazine. This reaction has been applied for the preparation of tetrazole derivatives.

Keywords:

  • tetrazoles;
  • sodium azide;
  • ureas;
  • imidyl chlorides