77825-80-0Relevant academic research and scientific papers
Tandem Ir-catalyzed allylic substitution reaction of allyl sulfinates and isomerization
Xu, Qing-Long,Dai, Li-Xin,You, Shu-Li
supporting information; experimental part, p. 800 - 803 (2010/04/06)
(Chemical Equation Presented) An efficient method for the synthesis of trisubstituted vinyl sulfones is reported. Using the [lr(COD)Cl] 2/phosphoramidite ligand (L1)/DBU, trisubstituted vinyl sulfones could be synthesized from allyl sulfinates
Studies on Chiral Organo-Sulfur Compounds. II. Stereochemistry of Thermal Chiral Allyl Sulfinate-Sulfone Rearrangements
Hiroi, Kunio,Kitayama, Ryuichi,Sato, Shuko
, p. 2628 - 2638 (2007/10/02)
A highly efficient and general synthetic route to optically active sulfinates by the stereospecific boron trifluoride etherate-catalyzed esterification of sulfinamides was developed.Dramatic solvent effects were observed in the thermal transformation of allyl sulfinate derivatives to sulfones.Heating of chiral trans- and cis-allyl sulfinates, (S)-(-)-3a,c,e and (S)-(-)-3b,d,f, in N,N-dimethylformamide at 90-120 deg C provided chiral sulfones (S)-(+)- and (R)-(-)-5,6,7 in good yields, respectively, with exceedingly high stereospecificity. Keywords - asymmetric transfer; stereospecificity; chiral allyl sulfinate; chiral allyl sulfone; boron trifluoride etherate; thermolysis
Selenosulfonation: Boron Trifluoride Catalyzed or Thermal Addition of Selenosulfonates to Olefins. A Novel Regio- and Stereocontrolled Synthesis of Vinyl Sulfones.
Back, Thomas G.,Collins, Scott
, p. 3249 - 3256 (2007/10/02)
Se-Phenyl areneselenosulfonates 1 add to a variety of olefins to produce β-phenylseleno sulfones 2.The reaction may be performed in the presence of boron trifluoride etherate to produce chiefly or exclusively Markovnikov products arising from a stereospecific anti addition.Alternatively, the addition may be thermally induced to afford anti-Markovnikov products generated by a nonstereospecific free-radical process.The two modes of addition achieve complementary regiospecificity.The β-phenylseleno sulfones are converted in high yield to vinyl sulfones by stereospecific oxidation-elimination with m-chloroperbenzoic acid.
