AN OLEFIN POLYANION EQUIVALENT: A NEW OLEFIN SYNTHESIS FROM TRIFLONES

Article abstract of DOI:10.1016/S0040-4039(01)91214-6

α-Trifyl-dimethylsulfone (CF3SO2CH2SO2CH3) is a reagent which allows successive polyalkylation of the two carbons with regiocontrol.The polyalkylated trifyl-sulfone then undergoes a Ramberg-Baecklund reaction with loss of triflinate anion and extrusion of SO2 to form an olefin.In synthetic terms the net structural change is equivalent to regiospecific alkylation of an olefin polyanion, =C==C=.