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Bamford-Stevens Reaction

(Bamford-Stevens Olefination)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr046

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Bamford-Stevens Reaction. Comprehensive Organic Name Reactions and Reagents. 46:195–201.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

This reaction is the transformation of ketones and aldehydes into alkenes through the base-promoted thermal or photolytic decomposition of p-toluenesulfonylhydrazones of the corresponding ketones or aldehydes and is known as the Bamford–Stevens reaction. This reaction is also referred to as the Bamford–Stevens olefination. This reaction has wide applications in the preparation of alkenes. Strong bases have been used in this reaction. The alkenes that have been formed during this reaction are normally the thermodynamic product, i.e., the highly substituted alkenes, and depending on the reaction conditions (e.g., bases used, solvents), other types of products rather than alkenes can also be prepared.

Keywords:

  • p-toluenesulfonylhydrazones;
  • alkenes;
  • butyl lithium;
  • diazo compounds