93915-91-4Relevant academic research and scientific papers
AN OLEFIN POLYANION EQUIVALENT: A NEW OLEFIN SYNTHESIS FROM TRIFLONES
Hendrickson, James B.,Boudreaux, Gerald J.,Palumbo, Paul S.
, p. 4617 - 4618 (1984)
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=.
Nuclear Synthons: Mesyltriflone as an Olefin Polyanion Equivalent
Hendrickson, James B.,Boudreaux, Gerald J.,Palumbo, Paul S.
, p. 2358 - 2366 (2007/10/02)
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.
