Nuclear Synthons: Mesyltriflone as an Olefin Polyanion Equivalent

Article abstract of DOI:10.1021/ja00269a037

Mesyltriflone (CF3SO2CH2SO2CH3) is developed as a nuclear synthon reagent capable first of multiple constructions such as alkylations then of Ramberg-Baecklund elimination to a substituted olefin.The alkylations are clean and regiospecific, often amenable to one-pot operation, and in most cases the elimination is smooth.A variety of examples is presented to establish the scope of the method, and the mechanism and stereochemistry are discussed.