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Reactions of Thianthrene Cation radical Perchlorate with 1-Alkyl-4-Arenesulfonylaminobenzenes

  • Noh, Jae-Sung (Department of Chemistry, Seoul National University) ;
  • Lee, So-Ha (Department of Chemistry, Seoul National University) ;
  • Kim, Kyong-Tae (Department of Chemistry, Seoul National University)
  • Published : 1988.06.20

Abstract

Reaction of thianthrene cation radical perchlorate (1) with 1-methyl-4-benzenesulfonylaminobenzene (10) afforded thianthrene (5), N-(4-tolyl)-N-thianthrenylbenzenesulfonamide (14), 1-methyl-3-[N-(4-tolyl)-N-benzenesulfonyl-amino- 4-benzene-sulfonylaminobenzene (16), cis-thianthrene-5,10-dioxide (17), 5-(3'-methyl-6-benzenesulfonylaminobenzene)thian threnium perchlorate (18), and benzenesulfonate. In the meantime, reaction of 1 with 1-ethyl-4-benzenesulfonylaminobenzene (12) afforded 5, 1-ethyl-3-[N-(4-ethylphenyl)-N-benzenesulfonyl]a mino-4-benzenesulfonylaminobenzene (19), 1-benzenesulfonyl-amino-4-[1-(2-benzenesulfonyla mino-5-ethylphenyl)ethyl]benzene (20), and 1-(1-acetamidoethyl)-4-benzenesulfonylaminobenz ene (21). The formations of these products except for 18 and benzenesulfonate could be rationalized by assuming a sulfonamidyl radical as an intermediate.

Keywords

References

  1. The Chemistry of the Sulphonium Group Organosulphur cation radicals H. J. Shine;C. J. M. Stirling(ed.)
  2. Bull. Korean Chem. Soc. v.4 J. S. Noh;K. Kim
  3. Korean Chem. Soc. v.25 S. H. Kim;K. Kim
  4. J. Chem. Soc. E. A. C. Lucken
  5. J. Am. Chem. Soc. v.94 Y. Murata;H. J. Shine
  6. Handbuch der Organischen Chemie v.12 Beilsteins
  7. Ceskoslov. farm. v.8 Z. Budesinsky;A. Emr;V. Musil;A. Svab;E. Zikmund
  8. J. Am. Chem. Soc. v.77 H. Gilmann;D. R. Swaympati
  9. Ber. v.65 E. Bergmann;M. Tschudnowsky
  10. J. Org. Chem. v.36 J. J. Silber;H. J. Shine
  11. J. Org. Chem. v.39 K. Kim;V. J. Hull;H. J. Shiite
  12. J. Org. Chem. v.48 S. Fujita
  13. J. Chem. Soc., Perkin A. R. Forrester;E. M. Johansson;R. H. Thomson
  14. J. Am. Chem. Soc. v.73 R. Adams;R. A. Wankel
  15. J. Am. Chem. Soc. v.73 R. Adams;J. H. Looker
  16. Bull. Chem. Soc. Jap. v.44 T. Okashi;M. Okahara;S. Komori
  17. J. Org. Chem. v.44 H. Teeninga;B. Zomer;J. B. F. N. Engberts
  18. J. Chem. Soc., Perkin I P. S. Dewar;A. R. Forrester;R. H. Thomson
  19. J. Org. Chem. v.34 R. S. Neale;N. L. Marcus
  20. Bull. Korean Chem. v.5 J. Shin;K. Kim
  21. J. Korean Chem. Soc. v.2 J. Shin;K. Kim
  22. J. Org. Chem. v.28 K. Sugiyama;H. J. Shine
  23. Bull. Korean Chem. Soc. v.6 H. S. Y oon;K. Kim
  24. Bull. Korean Chem. Soc. v.6 J. M. Lee;K. Kim;J. H. Shin
  25. J. Am. Chem. Soc. v.102 W. Ando;Y. Kabe;S. Kobayashi;C. Takyu;A. Yamagishi
  26. J. Am. Chem. Soc. v.93 C. S. Foote;J. W. Peters
  27. CA v.54 Z. Budesinsky;A. Emr;V. Musil;A. Svab;E. Zikmund

Cited by

  1. ChemInform Abstract: Reactions of Thianthrene Cation Radical Perchlorate with 1‐Alkyl‐4‐arenesulfonylaminobenzenes. vol.20, pp.1, 1989, https://doi.org/10.1002/chin.198901178
  2. An overview of some reactions of thianthrene cation radical. Products and mechanisms of their formation vol.27, pp.6, 1988, https://doi.org/10.1080/17415990600987965