New Methodology for the Conversion of Epoxides to Alkenes

Abstract Epoxides have been transformed in good yields to alkenes by a process involving (i) ring‐opening of the epoxide with 2‐mercaptobenzothiazole, (ii) oxidation of the derived β‐hydroxy thioethers to the corresponding sulfones, and (iii) thermal or base‐promoted fragmentation of these sulfones to alkenes. The stereochemistry of the starting epoxide is transferred faithfully to the alkene product, because of the SN2 epoxide ring‐opening reactions and the antiperiplanar SO2 elimination reaction of the β‐alkoxysulfinate intermediates. This methodology may form the basis of a new protecting group strategy for alkenes.