A study of compounds related to diaryl 2:2'-disulphonic acids

Abstract

The object of this work was to synthesise cyclic 2:2'-disulphides in the diphenyl series. Five series were studied, namely, diphenylene, 4:4':6:6'-tetramethyldiphenylene, 5:5' -dimethyldiphenylene, 4:4l -dimethyldiphenylene and 1:1'-dinaphthylene, paying particular attention to the action of reducing agents on the respective 2:2'-disulphonyl chlorides. The chemistry of the second series was studied more closely as it differed in a number of ways from that of the other series. The formation of dibenzothiophens from the disulphides and the disulphoxides was investigated and the constitution of some of the thiophens was proved by different syntheses. The optical resolution of 4:4' :6:6'-tetramethyldiphenyl-2:2'-disulphonic acid through its strychnine salt was achieved and the effect of added water to an ethanolic solution of the optically active sodium salts investigated. Finally both (+) and (-) 4:4':6:6'-tetramethyldiphenyl-2:2*-disulphonyl chlorides were obtained and from them the corresponding anilides.