1235335-05-3Relevant articles and documents
BCl3-mediated ene reaction of sulfur dioxide and-unfunctionalized alkenes
Markovic, Dean,Volla, Chandra M. R.,Vogel, Pierre,Varela-Alvarez, Adrian,Sordo, Jose A.
supporting information; experimental part, p. 5969 - 5975 (2010/09/04)
The first ene reactions of SO2 and unfunctionalized alkenes are reported. Calculations suggest that the endergonic ene reactions of SO 2 with alkenes can be used to generate β,γ-unsaturated sulfinyl and sulfonyl compounds. Indeed, in the presence of one equivalent of BCl3, the unstable sulfinic acid form stable sulfinic acid-BCl 3 complexes that can be reacted in situ with NCS to generate corresponding sulfonyl chlorides, or with a base to generate corresponding sulfinates. The latter can be reacted with electrophiles to generate sulfones, or with silyl chloride to form β,γ-unsaturated silyl sulfinates. The sulfinic acid-BCl3 complexes can be reacted with ethers that act as oxygen nucleophiles to produce corresponding sulfinic esters. Thus one-pot, three-component synthesis of β,γ-unsaturated sulfonamides, sulfinyl esters and sulfones have been developed starting from alkenes and sulfur dioxide (reagent and solvent).
