TheGrieco elimination is anorganic reaction describing theelimination reaction of an aliphaticprimary alcohol through aselenide to aterminal alkene.[1][2] It is named forPaul Grieco.
The alcohol first reacts witho-nitrophenylselenocyanate andtributylphosphine to form aselenide via anucleophilic substitution on the electron-deficientselenium. In the second step, the selenide is oxidized withhydrogen peroxide to give aselenoxide. This structure decomposes to form an alkene by anEi elimination mechanism with expulsion of aselenol in a fashion similar to that of theCope elimination. This reaction takes part in the synthesis of ring C of theDanishefsky Taxol synthesis.
The elimination step is common with the Clive-Reich-Sharpless olefination that uses PhSeX as the selenium source.[3]