77825-83-3Relevant academic research and scientific papers
A one-pot regioselective synthetic route to vinyl sulfones from terminal epoxides in aqueous media
Chawla, Ruchi,Kapoor, Ritu,Singh, Atul K.,Yadav, Lal Dhar S.
experimental part, p. 1308 - 1313 (2012/06/01)
A highly efficient LiBr catalysed regioselective synthesis of vinyl sulfones from readily available terminal epoxides and sodium sulfinates in a one-pot procedure using water as a reaction medium is reported. The protocol is adorned with several attributes of green chemistry like recycling of the catalyst, atom-economy and an aqueous medium.
Polystyrene-supported selenosulfonates: Efficient reagents for regio- and stereocontrolled synthesis of vinyl sulfones
Qian,Huang
, p. 1913 - 1916 (2007/10/03)
Two novel polystyrene-supported selenosulfonates reagents have been developed. As reagents for boron trifluoride catalyzed or AIBN catalyzed addition to olefins were successfully demonstrated and have been used for regioselective synthesis of vinyl sulfon
Decarboxylative radical addition to vinylsulphones and vinylphosphonium bromide: Some further novel transformations of geminal (pyridine-2-thiyl) phenylsulphones
Barton,Boivin,Crepon nee da Silva,Sarma,Togo,Zard
, p. 7091 - 7108 (2007/10/02)
Irradiation of O-acyl derivatives 1 of N-hydroxy-2-thiopyridone with visible light in the presence of phenyl vinyl sulphone or vinyl triphenylphosphonium bromide leads to the corresponding adducts 8 and 9 which can undergo a wide variety of further transformations.
SOME FURTHER NOVEL TRANSFORMATIONS OF GEMINAL (PYRIDINE-2-THIYL) PHENYLSULPHONES
Barton, Derek H. R.,Boivin, Jean,Sarma, Jadab,Silva, Elisabeth da,Zard, Samir Z.
, p. 4237 - 4240 (2007/10/02)
Geminal (pyridine-2-thiyl) phenylsulphones, obtained by decarboxylative radical addition of O-acyl derivatives of N-hydroxy-2-thiopyridone onto phenyl vinyl sulphone, undergo a wide variety of further transformations when subjected to sodium telluride or to organoaluminum reagents.
An Indirect Method for Engaging Unactivated Alkenes as Effective Dienophiles in Regioselective Diels-Alder Reactions
Paquette, Leo A.,Crouse, Gary D.
, p. 141 - 142 (2007/10/02)
Terminal alkenes and cyclic olefins can be made to enter into efficient, regiocontrolled Diels-Alder cycloaddition by prior selenosulfonation and oxidation to the vinyl sulfone.Reductive desulfonation after condensation with an activated diene provides th
Regiocontrolled Synthesis of Mono-, Di, and Trisubstituted Cyclohexenones by Cycloaddition of Vinyl Sulfones to 1-Methoxy-3--1,3-butadienes. Conversion of Alkenes into Effective Dienophilic Reagents
Kinney, William A.,Crouse, Gary D.,Paquette, Leo A.
, p. 4986 - 5000 (2007/10/02)
Cycloaddition of phenyl vinyl sulfone to Danishefky's diene followed by direct ketalization provided 7, a synthon for the 4-(2-cyclohexenyl) anion.Thus, 7 readily undergoes regiospecific γ-alkylation.Ensuing reductive desulfonylation and hydrolysis provides 2-(and 3-)-cyclohexenones efficiently.Zingiberenol, a monocyclic sesquiterpene, was prepared by means of this methodology.Terminal alkenes and cyclic olefins enter into comparable regiocontrolled Diels-Alder addition if they are first subjected to selenosulfonation and oxidation to the vinyl sulfone.Removal of the phenylsulfonyl substituent after condensation provides the adducts which are formally derived from alkylation of the hypothetical C5 anion of 2-cyclohexenone.The scheme can be expanded to include γ-alkylation prior to desulfonylation.By this means, one is able to prepare 4,5-disubstituted 2-(and 3-)cyclohexenones where the nature of the pendant side chains can be widely varied.
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.
