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Barton-Kellogg Olefination

(Barton-Kellogg Olefin Synthesis; Barton-Kellogg Reaction)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr056

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Barton-Kellogg Olefination. Comprehensive Organic Name Reactions and Reagents. 56:249–253.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

Coupling of two ketones into alkenes, particularly applicable to the synthesis of moderately to highly hindered alkenes, is generally referred as Barton-Kellogg olefination. In this reaction, the steric constraints are gradually introduced via sequential processes involving a 1,3-Dipolar Cycloaddition to form five-membered Δ3-1,3,4-thiadiazoline, followed by the nitrogen elimination to three-membered episulfide, and finally the sulfur extrusion to afford the alkenes. Although this reaction can be used for the synthesis of asymmetric alkenes from two different ketones, symmetric alkenes will always be formed as by-products.

Keywords:

  • Δ3-1,3,4-thiadiazoline;
  • alkenes;
  • steric constraints;
  • olefination mechanism