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Tiemann Rearrangement

(Tiemann Amidoxime-Urea Rearrangement)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr622

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Tiemann Rearrangement. Comprehensive Organic Name Reactions and Reagents. 622:2773–2776.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The Beckmann or Lossen type rearrangement of amidoximes into the corresponding substituted ureas when treated with benzenesulfonyl chloride or acetic anhydride followed by hydrolysis, is generally referred to as the Tiemann rearrangement or the Tiemann amidoxime-urea rearrangement. The study discusses the occurance of Tiemann rearrangement in the amidoxime and benzamidoxime. Furthermore, the coexistence of NH2 and NOH groups in amidoxime has been characterized and two tautomers, the amino iminoxime have been found to predominate. This reaction has general applications in the preparation of substituted ureas as well as cyanamides, oxathiadiazoles, and carbodiimides.

Keywords:

  • amidoxime;
  • benzamidoxime;
  • benzenesulfonyl chloride;
  • N,N′-diphenylurea