25093-89-4Relevant articles and documents
Copper Triflate Mediated α-Monohalogenation of α-Diazo β-Ketosulfones with Ammonium Halides
Chan, Chieh-Kai,Wang, Heui-Sin,Hsu, Ru-Ting,Chang, Meng-Yang
, p. 2045 - 2056 (2017/04/26)
Copper triflate mediated α-monohalogenation of α-diazo β-ketosulfones with ammonium halides provides the corresponding α-halo β-ketosulfones. Different metal triflates are investigated for this facile and efficient transformation. A plausible mechanism is proposed.
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.