37557-96-3Relevant academic research and scientific papers
Chemoselective mono halogenation of β-keto-sulfones using potassium halide and hydrogen peroxide; synthesis of halomethyl sulfones and dihalomethyl sulfones
Suryakiran,Prabhakar,Srikanth Reddy,Chinni Mahesh,Rajesh,Venkateswarlu
, p. 877 - 881 (2007/10/03)
The synthesis of α-halo β-keto-sulfones using potassium halide and hydrogen peroxide as a chemoselective mono halogenation reagent and the synthesis of α,α-symmetrical and asymmetrical dihalo β-keto-sulfones and α-halo, α-alkyl and β-keto-sulfones is described. Base induced cleavage of α-halo β-keto-sulfones, α,α-dihalo β-keto-sulfones, and α-halo, α-alkyl β-keto-sulfones afforded the corresponding halomethyl sulfones, dihalomethyl sulfones and haloalkyl sulfones.
Sulfonyl esters. 3. The formation of sulfone-sulfonates in the reactions of aryl methanesulfonates with sodium borohydride
Baum, James Clayton,Durkin, Kathleen Anne,Precedo, Laura,O'Blenes, Stacy Brian,Goehl, John Edward,et al.
, p. 2127 - 2135 (2007/10/02)
Sodium hydride reductions of aryl methanesulfonates afford dimeric sulfone-sulfonate esters as well as products arising from SO bond rupture.SO bond rupture becomes more competitive as the LUMO energy of the sulfonate ester declines.Exploration of the chemistry of a sulfone-sulfonate ester revealed a complex novel reaction that resulted in the formation of, inter alia, a dichloromethanesulfonate ester and a trichloromethanesulfonate aster.The first succesful approaches to the synthesis of the heretofore unknown trichloromethanesulfonates and dichloromethanesulfonates are reported.Key words: sodium hydride reductions, sulfenes, sulfone-sulfonate esters.
Mechanism in the chlorinolysis of sulfinyl chlorides
Ahern, Terence Patrick,Haley, Michael Francis,Langler, Richard Francis,Trenholm, June Ellen
, p. 610 - 614 (2007/10/02)
The successful synthesis and chlorinolysis of α-mercaptodimethyl sulfone have provided additional support for our contention that Pummerer rearrangements may occur during the chlorinolyses of α-sulfonyl sulfinyl chlorides.Further exploration of chlorinolyses of α-sulfonyl systems has uncovered the first observation of CS bond cleavage during the chlorinolyses of (i) a sulfinyl chloride and (ii) a sulfinate ester.
THE PREPARATION, SPECTRAL PROPERTIES, STRUCTURES, AND BASE-INDUCED CLEAVAGE REACTIONS OF SOME α-HALO-β-KETOSULFONES
Grosset, Stuart J.,Dubey, Pramod K.,Gill, Glen H.,Cameron, Stanley T.,Gardner, Patrick A.
, p. 798 - 807 (2007/10/02)
The halogenation of β-ketosulfones such as α-methylsulfonylacetophenone (1) and benzenesulfonylacetone (10) can be effected with sulfuryl chloride or pyridinium bromide perbromide.Regiochemical control can be achieved by control of stoichiometry and/or the reaction conditions.Detailed 1H and 13C nmr, and mass spectra are recorded for a series of halogenated β-ketosulfones, together with structures by X-ray crystallography for 1, 2-chloro-2-methylsulfonyl-1-phenylethanone (2), chloromethyl methyl sulfone (4), and α-chloroacetophenone (21).Results from these studies are used to suggest a reason for the difficulty associated with substitution reactions of α-halosulfones.
The synthesis and chlorinolysis of 5-phenyl-2,4,5-trithiapentane-2,2-dioxide
Ahern, Terence Patrick,Langler, Richard Francis,McNeil, Robert Leonard
, p. 1996 - 1998 (2007/10/02)
Application of mercaptide anions to the dechlorination of an α-polychlorosulfonyl substrate has provided the key step in a successful synthesis of the title compound. 5-Phenyl-2,4,5-trithiapentane-2,2-dioxide undergoes chlorinolysis in an aqueous medium to yield products consistent with the view that α-sulfonyl oxodichlorosulfonium chlorides and α-sulfonyl dichlorosulfonium chlorides may undergo unusually facile Pummerer rearrangements.
