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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. 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