117365-59-0Relevant articles and documents
A Stereospecific Synthesis of Trisubstituted Alkenes via Hydridation of Dialkylhaloboranes Followed by Hydroboration-Iodination of Internal Alkynes
Brown, Herbert C.,Basavaiah, D.,Kulkarni, Surendra U.
, p. 171 - 173 (1982)
Dialkylvinylboranes, prepared conveniently via the hydridation of dialkylhaloboranes in the presence of an internal alkyne, react with iodine under basic conditions to produce trisubstituted alkenes of established stereochemistry, providing a general synthesis of trisubstituted alkenes with unambiguous stereochemistry.
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.
Organic synthesis with sulfones no. XXXV. Iron catalysed condensation and hydrogenolysis of vinylic sulfones with Grignard reagents. A stereoselective synthesis of di- and trisubstituted olefins
Fabre, Jean-Luc,Julia, Marc,Verpeaux, Jean-Noel
, p. 772 - 778 (2007/10/02)
Vinylic sulfones are readily available in the E or Z configuration.Condensation with primary Grignard reagents occurs stereospecifically in the presence of iron catalysts, leading to trisubstituted olefins.With secondary Grignards stereospecific hydrogenolysis to 1,2-disubstituted olefins is observed.