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Truce-Smiles Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr628

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Truce-Smiles Rearrangement. Comprehensive Organic Name Reactions and Reagents. 628:2803–2806.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The Truce-Smiles rearrangement is an extension of the Smiles rearrangement and this rearrangement stands for the migration of an aryl group of diaryl sulfones when treated with a strong base, such as the rearrangement of mesityl p-tolyl sulfone to 2-(4?-methylbenzyl)-4,6-dimethylbenzenesulfinic acid and the rearrangement of phenyl p-tolyl sulfone to o-benzylbenzenesulfinic acid. This rearrangement is generally carried out under two distinct conditions: metalation of diaryl sulfones by BuLi in ether and by KOBut in DMSO. Under both conditions, the three isomers of mesityl tolylsulfones give three different products with retention of the tolyl orientations. Furthermore, mesityl β-naphthyl sulfone gives only 5% of rearrangement product under n-BuLi/ether conditions. Several other aromatic sulfones undergo a similar rearrangement. The rearrangement of aryl sulfones has been extended to aryl alkyl sulfones. This rearrangement has certain application in the preparation of aromatic sulfinic acids.

Keywords:

  • phenyl p-tolyl sulfone;
  • o-benzylbenzenesulfinic acid;
  • mesityl β-naphthyl sulfone;
  • o-neopentylbenzenesulfinic acid