Alkylthio-sulphonium Salts

Alkylthio-sulphonium Salts.— Admirably thorough studies have been made by Caserio and her co-workers on the preparation and reactions of alkylthio-sulphonium salts, which are now being recognized as intermediates in a number of organosulphur reactions. 

Mej OCOCFj CFjCOr - Me SsR CFjCO 2 are direct methods of synthesis. 

A bis(arylthio)sulphonium salt, probably better represented as the symmetrical cation (19), is formed either from a disulphide or from an arenesulphenyl chloride with SbCU.  

Tanikaga, K. Tanaka, and A. Kaji, J. Chem. Soc., Chem. Commm., 197S, 865. 

4 proceeds via methylthio-sulphonium ions, which rearrange by cleavage and re formation of C—S and S—S bonds by way of an a-(methylthio)carbonium ion.  

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Conversions of thiols into disulphides and thiolsulphonates through their reactions with DMSO and TFAA involve the alkylthio-sulphonium salts as intermediates, the thiolsulphonate arising when water is present/ Bis-(arylthio)sulphonium salts are effective reagents for the conversion of alkenes into thiirans/ ... 

Anodic oxidation of dithioacetals gives the disulphide, rather than the expected sulphoxide, sulphone, or sulphonium salt (Scheme 5). Further oxidation to the thiolsulphonate can be brought about by prolonged electrolysis. Di-t-butyl peroxide initiates a homolytic 1,2-shift so as to put another carbon atom between the alkylthio-groups in a dithioacetal, resulting in a l,3-bis(alkylthio)alkane... 

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