Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthesis and Decomposition of Alkane- and Arenesulfonyl Aryl Disulfides
Yasuo AbeTakeshige NakabayashiJitsuo Tsurugi
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1971 Volume 44 Issue 10 Pages 2744-2749

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Abstract

Pyridinium alkane- and arenethiolsulfonates were allowed to react with arenesulfenyl chlorides, CISAr′, to yield sulfonyl disulfides in which R is n-dodecyl, benzyl, phenyl, or p-tolyl group, and Ar′ o-nitrophenyl or o-nitro-p-chlorophenyl. p-Toluenesulfonyl p-nitrophenyl disulfide was also prepared by this method. IR and UV spectra of these compounds were determined and compared with those of the corresponding thiolsulfonates. Decomposition of 35S-labeled p-toluenesulfonyl p-nitrophenyl disulfide, p-CH3C6H4SO2S35SC6H4NO2-p, gave 35S-labeled p-nitrophenyl p-toluenethiolsulfonate, p-CH3C6H4SO235SC6H4NO2-p. Triphenylphosphine was found to attack two oxygen atoms and a sulfur atom of p-toluenesulfonyl o-nitrophenyl disulfide at the same rate. The reaction of triphenylphosphine with 35S-labeled p-toluenesulfonyl o- and p-nitrophenyl disulfides revealed that the central sulfur atom of these sulfonyl disulfides was desulfurated. This result coincides with that of the decomposition mentioned above. The susceptibility of sulfonyl disulfides containing p-nitrophenyl group to the decomposition and the desulfuration of the central sulfur atom of sulfonyl disulfides in general are also discussed.

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