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Desulfonylation Reactions

  1. Diego A. Alonso,
  2. Carmen N Ájera

Published Online: 16 MAR 2009

DOI: 10.1002/0471264180.or072.02

Organic Reactions

Organic Reactions

How to Cite

Alonso, D. A. and Ájera, C. N. 2009. Desulfonylation Reactions. Organic Reactions. 72:2:367–656.

Author Information

  1. University of Alicante, Department of Organic Chemistry and Institute of Organic Synthesis (ISO), Faculty of Science, Alicante, Spain

Publication History

  1. Published Online: 16 MAR 2009

Abstract

The use of sulfones in organic chemistry, acting as an auxiliary group, is still a very important synthetic strategy, especially for the formation of carbon-carbon single and double bonds. Once the synthetic objective is achieved, the sulfone gruop is usually removed from the molecule. This removal most commonly involves a reductive desulfonylation process with either replacement of the sulfone by hydrogen, or a process that results in the formation of a carbon-carbon double bond when a β-hydroxy or β-alkoxy sulfone is employed.

This chapter is devoted to the replacement of the sulfone group by a hydrogen (reductive desulfonylation reactions), and reductive elimination reactions of Julia-type substrates (Julia-Lythgoe olefination process). The chapter addresses the full scope, generality, limitations, and synthetic applications of these reactions. The literature through most of 2007 is covered.

Keywords:

  • Amination Reagents;
  • Aromatic amine synthesis;
  • Aliphatic amine synthesis