Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Reactions of Thianthrene Cation Radical Perchlorate with N-(p-Methoxyphenyl)benzene- and Methanesulphonamides

  • Sung Hoon Kim (Department of Chemistry, Seoul National University) ;
  • Jung Hyu Shin (Department of Chemistry, Seoul National University) ;
  • Kyongtae Kim (Department of Chemistry, Seoul National University)
  • Published : 1989.12.20
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Abstract

Reactions of thianthrene cation radical perchlorate (1) with N-(p-methoxyphenyl)benzenesulphonamide (14) in acetonitrile at room temperature afforded various products : thianthrene (3), N-(p-hydroxyphenyl)benzenesulphonamide (16), benzenesulphonamide (18), hydroquinone (20); 5-(5-benzenesulphonamido-2-methoxyphenyl)-thia nthrenium perchlorate(21), 2-benzenesulphonamido-2'-hydroxy-5,5'-dimethoxy biphenyl(24), 2-benzenesulphonamido-2',5'-dihydroxy-5-methoxy -biphenyl(25), and a traceable amount of p-quinone(23). The formations of part of (3) and (21) can be explained by either disproportionation or half-regeneration mechanism but those of the remainders by diverse reactions of sulphonamidyl radical (27) derived from (14) (through single electron transfer, followed by deprotonation processes). Similar results were observed from the reaction with N-(p-methoxyphenyl)methanesulphonamide (15).

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References

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Cited by

  1. An overview of some reactions of thianthrene cation radical. Products and mechanisms of their formation vol.27, pp.6, 1989, https://doi.org/10.1080/17415990600987965