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Grieco elimination

Chemical reaction

Grieco elimination
Summary

Chemical reaction

The Grieco elimination

The Grieco elimination is an organic reaction describing the elimination reaction of an aliphatic primary alcohol through a selenide to a terminal alkene. It is named for Paul Grieco.

The alcohol first reacts with o-nitrophenylselenocyanate and tributylphosphine to form a selenide via a nucleophilic substitution on the electron-deficient selenium. In the second step, the selenide is oxidized with hydrogen peroxide to give a selenoxide. This structure decomposes to form an alkene by an Ei elimination mechanism with expulsion of a selenol in a fashion similar to that of the Cope elimination. This reaction takes part in the synthesis of ring C of the Danishefsky Taxol synthesis.

The elimination step is common with the Clive-Reich-Sharpless olefination that uses PhSeX as the selenium source.

References

References

  1. (1976). "Organoselenium chemistry. A facile one-step synthesis of alkyl aryl selenides from alcohols". [[J. Org. Chem.]].
  2. (1975). "Olefin synthesis. Rate enhancement of the elimination of alkyl aryl selenoxides by electron-withdrawing substituents". [[J. Org. Chem.]].
  3. (2011). "Organic Syntheses Based on Name Reactions: A Practical Guide to Over 800 Transformations.". Elsevier.
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

elimination-reactions olefination-reactions name-reactions
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