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Stieglitz Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr602

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Stieglitz Rearrangement. Comprehensive Organic Name Reactions and Reagents. 602:2673–2676.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The migration of a substituent (mostly the aryl group) in a series of nitrogen-containing molecules (e.g., hydroxylamines, amines, haloamines, azides) at the tertiary carbon to the adjacent nitrogen atom to form an imine derivative (primarily the Schiff base) is generally known as the Stieglitz rearrangement. This reaction takes place under various conditions, depending on the starting materials. The study finds that other acidic reagents, including phosphorus pentoxide and boron trifluoride, can also promote the Stieglitz rearrangement of triarylmethyl hydroxylamines. It has been found that the substrates of bridged bicyclic systems undergo the Stieglitz rearrangement much more easily. This reaction has useful applications, such as preparation of Schiff bases as well as some aromatic heterocycles.

Keywords:

  • p-nitrobenzenesulfonyl peroxide;
  • triarylmethylamines;
  • lead tetraacetate;
  • Schiff base