New synthesis of alkane- and arylsulfonyl chlorides by oxidation of thiols and disulfides with chlorine dioxide

Oxidative transformations of diisobornyl disulfide

“…9 Chlorine dioxide was success fully used in the synthesis of dialkyl and diaryl thiosul fonates, sulfonic acids, and sulfonyl chlorides. [10][11][12] In the present work, we first performed oxidation of terpene di sulfide with Pb(OAc) 4 and ClO 2 ; earlier we used MCPBA for oxidation of terpene disulfides bearing menthane and neomenthane moieties. 13 Oxidation of disulfide 1 with 1 equiv.…”

“…Depending on the molar reactant ratio, the corresponding sulfinic (12,13) or sul fonic (14,15) esters were obtained. NMR spectra of sulfin ic esters 12 and 13 contain two sets of the signals for the isobornyl and alkoxy groups indicating the presence of two diastereomers.…”

“…Earlier, 17 we found that the order of the reactant mixing affected the structure of the products formed upon ClO 2 oxidation of 1 methyl 2 sulfanylimidazole. In the present (11); Et (12,14); Bu t (13,15) work, we also used two orders of the reactant mixing. In the first case, the gaseous ClO 2 was fed by doses into a solution of disulfide 1 (oxidation with a lack of the oxi dizer, method A); in the second case, a solution of disul fide 1 was added by doses to a solution of ClO 2 (oxidation with an excess of oxidizer, method B).…”

7.28 Oxidation of Sulfur, Selenium, and Tellurium

“…A more environmentally benign and cheaper oxidation of thiols or disulfides to sulfonamides is provided by TCCA in water followed by the addition of K 2 CO 3 and the proper amine. 102 The one-pot oxidative halogenation of thiols to sulfonyl chlorides and sulfonyl fluorides can be performed by other systems such as TMSCl/KNO 3 , 103 N-chlorosuccinimide (NCS), 104 ClO 2 ,105 or NaOCl/KHF 2 . 106 A useful application of the NaOCl/KHF 2 system is the selective synthesis of difficult-to-access heteroaryl sulfonamides from heteroaryl thiols.…”

Synthesis of 3-methylquinazolin-4(3H)-one derivatives

“…The latter is produced on a large scale for bleaching of cellulose and decontamination of water and was shown to be a convenient and efficient oxidant ensuring transformation of alkane-and arenethiols into disulfides [2], S-alkyl thiosulfonates [3], and sulfonyl chlorides [4]. Oxidation of heterocyclic thiols with ClO 2 was not studied.…”