Standard Article

You have free access to this content

Eastwood Olefination

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr204

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Eastwood Olefination. Comprehensive Organic Name Reactions and Reagents. 204:949–951.

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

Eastwood olefination reaction was initially reported by Grank and Eastwood in 1964. It is the stereospecific preparation of olefin from vicinal diol by means of the thermal decomposition of a five-membered cyclic orthoformate of the diol in the presence of a catalytic amount of acid (e.g., acetic acid). Therefore, this reaction is known as the Eastwood procedure or Eastwood deoxygenation procedure but is called Eastwood olefination in this work. It has been reported that using acetic anhydride as a solvent, the cyclic orthoformate can be converted into olefin in a high yield. This improvement is referred to as Ando's modification. The Eastwood olefination is especially helpful in the preparation of dideoxy nucleosides and nucleotides. Because acetic anhydride might cause the cleavage of the N-glycosyl bond, dideoxy thymidine has been prepared using hydrous zirconium oxide as the catalyst and tributylamine as the stabilizer.

Keywords:

  • Eastwood olefination;
  • olefin;
  • thermal decomposition;
  • Ando's modification;
  • solvent;
  • nucleotides