62872-77-9Relevant academic research and scientific papers
Organic synthesis with sulphones no. XXXIV. Uncatalysed addition versus nickel catalysed coupling reaction of vinylic sulfones with Grignard reagents. A stereoselective synthesis of olefins and dienes
Fabre, Jean-Luc,Julia, Marc,Verpeaux, Jean-Noel
, p. 762 - 771 (2007/10/02)
Grignard reagents undergo Michael addition to vinylic sulfones.With a β-β-disubstituted vinylic sulfone an unexpected dimer is obtained.Under nickel catalysis methyl, aryl and alkenyl Grignard reagents displace the sulfonyl group of the readily available α,β-unsaturated sulfones.Methyl, resp. phenyl substituted olefins or conjugated dienes are formed.Under appropriate conditions the reaction proceeds with complete retention of configuration.
Selective alkylation of allyl phenyl sulphone. A novel synthesis of alk-2-enes
Savoia, Diego,Trombini, Claudio,Umani-Ronchi, Achille
, p. 123 - 125 (2007/10/12)
Treatment of the lithium salt of allyl phenyl sulphone (1) with a variety of alkyl halides affords exclusively α-alkylated products (2a-d). which are easily isomerized to (E)-αβ-unsaturated phenyl sulphones (4a-d) with catalytic amounts of t-butoxide. A new, simple method of reductive cleavage of the carbon-sulphur bonds of compounds (2)-(4) with potassium-graphite (C8K) is described, providing a general route to alk-2-enes [(5) and (6)] in satisfactory yields.
