Published Online: 15 SEP 2010
Copyright © 2010 John Wiley & Sons, Inc. All rights reserved.
Comprehensive Organic Name Reactions and Reagents
How to Cite
2010. Eastwood Olefination. Comprehensive Organic Name Reactions and Reagents. 204:949–951.
- Published Online: 15 SEP 2010
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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.
- Eastwood olefination;
- thermal decomposition;
- Ando's modification;