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.
Paul Grieco is an organic chemist at Montana State University. His research focuses on the total synthesis of natural products and the study of solvent effects in various organic reactions. He has received several awards for his work, including the American Chemical Society (ACS) Arthur C. Cope Scholar Award in 1990 and the ACS Award for Creative Work in Synthetic Organic Chemistry in 1991. Among his contributions are two name reactions: the Grieco elimination and the Grieco three-component condensation.
