53066-72-1Relevant articles and documents
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.
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.
