24454-33-9Relevant academic research and scientific papers
NUCLEOPHILIC ADDITIONS TO α,β-UNSATURATED SULPHONES. IV. ADDITION-DESULPHONYLATION IN THE REACTIONS OF VINYL SULPHONES BEARING A β CARBONYL FUNCTION
Benedetti, Fabio,Fabrissin, Silvio,Fagotto, Roberto,Risaliti, Amerigo
, p. 613 - 618 (2007/10/02)
Reactions of oxygen, nitrogen and carbon nucleophiles with β-methoxycarbonylvinyl phenyl sulphone, 1, β-acetylvinyl phenyl sulphone, 2, and 3-phenylsulphonylcyclopentenone, 3, have been investigated.The addition of methanol and pyrrolidine to the sulphone 1 is followed by elimination of benzenesulphinate, in analogy with earlier observations on β-substituted α,β-unsaturated sulphones.Elimination of sulphinate is also observed, for the first time, in the reaction of 1 and 2 with cycloalkanone enamines.The cyclic keto sulphone 3, on the contrary, reacts with a cyclopentanone enamine to give a cyclobutane adduct in which the sulphone group is retained.
