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The Chapman Rearrangement

  1. J. W. Schulenberg,
  2. S. Archer

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or014.01

Organic Reactions

Organic Reactions

How to Cite

Schulenberg, J. W. and Archer, S. 2011. The Chapman Rearrangement. Organic Reactions. 14:1:1–51.

Author Information

  1. Sterling-Winthrop Research Institute, Rensselaer, New York

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

The thermal conversion of aryl N-arylbenzimidates to N-aroyldiphenylamines is known as the Chapman rearrangement. The starting materials for the Chapman rearrangement have been referred to as imino ethers, imido esters, imidates, and by miscellaneous other names. Roger and Neilson have named all the compounds as imidates. This chapter does not name the rearrangement products according to Chemical Abstracts, which lists the compounds as derivatives of benzanilide or benzamide. Here the products are called aroyldiarylamines. All of the compounds obtained by amide hydrolysis are named diarylamines. The Chapmann rearrangement has been shown to be an intramolecular reaction in which a 1,3 shift of an aryl group from oxygen to nitrogen occurs.

Keywords:

  • Chapman rearrangement;
  • diphenyl-2-carboxylic acids;
  • acridones;
  • alkyl imidates;
  • catalyzed rearrangements;
  • thermal rearrangements;
  • experimental conditions