Hydrogen alkyl disulfide

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. ... 

Alcoholysis of the acyl organyl sulfides RC(0)SxR (R, R =alkyl, aryl x=2, 3) in the presence of hydrogen chloride gives the organyl hydrodi- and hydrotrisulfides RSxH (x=2,3) in good yield [20,21,65,176,282]. Acyl alkyl disulfides react with thiols to yield asymmetrical disulfides [200]. Selenium bis(thiocar-... 

Disulfides can be prepared by treatment of alkyl halides with disulfide ions and also indirectly by the reaction of Bunte salts (see 10-41) with acid solutions of iodide, thiocyanate ion, or thiourea, or by pyrolysis or treatment with hydrogen peroxide. Alkyl halides also give disulfides when refluxed with sulfur and NaOH, and with piperidinium tetrathiotungstate or piperidinium tetrathiomolybdate. ... 

Types of sulfur compounds fall into two main classes, the acidic compounds such as hydrogen sulfide and mercaptans, and the neutral compounds which include sulfides both alkyl and cyclic, thiophenes, and disulfides. 

Reductive amination of benzaldehyde with (R)-81 provided the corresponding benzyl amine, which was reductively alkylated with formaldehyde to give 82 (Scheme H) " Compound 82 was debenzylated by hydrogenation in the presence of Pearlman s catalyst to afford frovatriptan ((/J)-6). Alternatively, monomethylation of amine (/ )-81 was affected by treatment with carbon disulfide and dicyclohexylcarbodiimide in pyridine to provide isothiocyanate 83, which was reduced with sodium borohydride to give (l )-6. 

Irradiation of aliphatic thiols, sulfides, and disulfides with a mercury lamp produces gaseous products identified by the mass spectrograph. Thiols are the least stable to light, with the formation of hydrogen95-129 as the main product. Sulfides and disulfides yield, as the predominant products, saturated hydrocarbons of structures corresponding to the smallest alkyl radical attached to sulfur. Haines et al.95-97 have offered a mechanism to explain the predominant production of hydrogen during photolysis of thiols. 

Starting from 2-mercaptothiazoles 192 and 197, alkylation leads to the respective thioethers 485a-c (Scheme 128) and 489a,b (Scheme 129), whereas oxidation by hydrogen peroxide gives the disulfides and/or the parent compounds (e.g., 479 64BCJ1526 and 62BCJ1998, respectively). 

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