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Preparation and Reactions of Chlorodisulfanyl Derivatives of Carbonic Acid
Boehme, Horst,Brinkmann, Manfred,Steudel, Hans-Peter
, p. 1244 - 1251 (2007/10/02)
Chlorodisulfanes 4 have been prepared via chlorolysis of acetic alkoxy(dithioformic) anhydrides 2 or via the reaction of O-alkyl chloro(thioformate) 5 with sulfur dichloride.With sodium 4-toluenesulfinate exclusively the chlorosulfanyl function reacts to form the dichloro(alkoxy)methyldisulfanyl(4-methylphenyl)sulfones 7.The aluminium chloride catalysed elimination of ethyl chloride from 4 leads to chlorodisulfanylformyl chloride (8).The chlorocarbonyl function of 8 reacts with ethanol to give the ester 10, the halosulfanyl function of which further reacts with thiophenol, to give the trisulfide 11.Phenols on the other hand react with the chlorosulfanyl function of 8 under formation of ring substituted products 12 or 14; the chlorocarbonyl function of which can be converted with ethanol into ester 13 or with diethylamine into amide 15.Analogous reactions take place with 1,3,5-trimethoxybenzene to give 16 and 17, respectively.
