Puneet Varma

Grieco elimination

Updated on
Share on FacebookTweet on TwitterShare on LinkedIn
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.[1][2] 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.

References

Grieco elimination Wikipedia


Similar Topics
Boo Moon
Martine Baay Timmerman
Stefan Nadelman
Topics