The Preparation of α-Disulfones by Cobalt(III) Oxidation

Electrochemical Oxidation of Sulfinic Acids: Efficient Oxidative Synthesis of Diaryl Disulfones

“…It can be used for Michael addition reaction, [1][2][3] Diels-Alder reaction, 4 functional-group interconversion, 5,6 installation of heteroatom moieties, 5 C-C coupling reactions, 7,8 dimerization, 9 trimerization 10 and polymerization. 11 Diphenyl disulfones are already utilized in several chemical reactions as reagent for selective cleavage of methylprenyl (2,3-dimethylbut-2-en-1-yl), prenyl (3-methylbut-2-en1-yl), and methallyl (2-methylallyl) ethers, 12 and as catalyst for isomerization of alkenes, 13,14 chemoselective cleavage of methylsubstituted allyl ethers, 15 photopolymerization of vinyl monomers, 16 Several methods have been reported for the synthesis of diphenyl disulfone derivatives, including the oxidation of benzensulfinic acid by KMNO 4 , 17 and Cobalt(III), 18 oxidation of 1,2-bis-(benzenesulfonyl)hydrazine by NaOCl in CHCl 3 , 19 thermal reaction of benzene and sulfur dioxide in the presence of benzoyl peroxide, 20 decomposition of phenylphenylsulfonyl diimide in p-xylene, 21 oxidation of diphenyl disulfide by hydrogen peroxide, 22 oxidation of N,N'-bis(benzenesulfonyl) hydrazide by sodium hypochlorite 23 or nitric acid, 24 reaction of sodium benzenesulfinate and benzenesulfonyl chloride, 25 and reduction of benzenesulfonyl chloride by samarium 26 or lithium. 27 However, these methods have the following disadvantages such as low yield, poor purity, lack of easy availability/preparation of the starting materials, tedious work-up, heavy metal pollution, strongly acidic media and safety problems.…”

Studies of sulfonyl radicals. 4. Flash photolysis of aromatic sulfones

“…(Calcd for CuH^ISOj: C, 45.69; H, 5.87 Found; C, 45.45; H, 5.51.) Diphenyl disulfone was synthesized according to the method of Denzer et al 18 Results and Discussion 1. Absorption Spectra of the Transient Species Produced by the Flash Photolysis of Arenesulfonyl Iodides.…”