Disulfides from Bunte salts

Sodium thiosulfate reacts with alkyl halides to form salts of the type RSSOjNa (Bunte salts). Alkyl disulfides may be obtained from these salts by pyrolysis or reaction with iodine or hydrogen peroxide. The yields range from 47% to 6S>%. Cyano and carboxyl groups do not interfere. Benzoylation of sodium thiosulfate produces benzoyl disulfide in 58% yield. ... 

Hydrolysis of the di-Bunte salt derived from 3,3-bis(chIoroniethyl)-oxetane and sodium thiosulfate gave either a tHaulfide or a probable disulfide, depending on conditions. The former, obtained by add hydrolysis of di-Bimte salt contaminated with sodium thioaulfate, wm a colorless crystalline compound, considered to be (LXXVl). The lat ter, from the action of dilute hydrochloric acid on the pure di-Bnnte salt, was a yellow oil which polymerized immediately on distillation and therefore no direct ovidDnoe on He strueturD vrtua obtained, oe... 

The reaction of S-2-(alkylamino)ethyl thiosulfates, applied in the form of zwitterionic Bunte salts, with carbon disulfide in aqueous sodium hydroxide produces intermediate dithiocarba-mates, which cyclize with loss of sulfite anion from the thiosulfate moiety to give 4-alkyl-5,6-di-hydro-l,2,4-dithiazine-3(4/f)-thiones.28... 

Reese and Eyring [45] have demonstrated that the reaction of sulfite with hair is a pseudo-hrst-order reaction. In other words, the chemical reaction of sulfite with the disulfide bond of hair is slower than diffusion of sulfite into hair. Elsworth and Phillips [46, 47] and Volk [48] examined the sulfi-tolysis of keratin, demonstrating that the rate of cystine cleavage is optimal at acid pH. Wolfram and Underwood [49] found a broad optimum for cystine cleavage by sulhte at pH 4 to 6. The decrease in cystine cleavage at acidic pH (below pH 4) is due to a decrease in the concentration of the nucleophilic sulhte species. On the other hand, the decrease in cystine cleavage as pH is raised (alkaline pH) results from alkaline hydrolysis of the Bunte salt [50]. 

Early work [108-110] showed that polymeric disulfides could be prepared from sodium polysulfide and organic dithiosulfates or di-Bunte salt ... 

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