95495-89-9Relevant academic research and scientific papers
Synthesis of 1-alkene-1,3-sultones from 2,3-epoxy-alkanesulfonyl chlorides
Bonini, Bianca F.,Kemperman, Gerjan,Willems, Sander T.H.,Fochi, Mariafrancesca,Mazzanti, Germana,Zwanenburg, Binne
, p. 1411 - 1413 (1998)
Dehydrochlorination of αβ-epoxy sulfonyl chlorides 3 leads to 1-alkene-1,3-sultones 1 most probably via epoxy sulfenes 2.
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).
