Corey-Winter Olefin Synthesis

Conversion Of 1,2-diols To Alkenes. The Cyclic Thiocarbonate Is Available From Reaction Of The Diol With Thiophosgene Or Thiocarbonyldiimidazole, And Reacts With Added trimethylphosphite via A syn-elimination To The Alkene.

Mechanism Of The Corey-Winter Olefin Synthesis

It Is Assumed That The Reaction Proceeds With Attack Of Phosphite On Sulphur Leading To A Carbene, Which May React With A Second Equivalent Of Phosphite During The Cycloreversion That Splits Out Carbon Dioxide And Yields The Product Alkene.