Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
권호 표지

Reaction of Thianthrene Cation Radical Perchlorate with Thioxanthene. Synthesis of Thioxanthene Derivatives

티안트렌 양이온 자유라디칼과 염소산염과 티오크잔틴의 반응. 티오크잔틴 유도체의 합성

  • Kyongtae Kim (Department of Chemistry, College of Natural Sciences, Seoul National University)
  • 김경태 (서울대학교 자연과학대학 화학과)
  • Published : 19800230

Abstract

The reaction of thianthrene cation radical perchlorate with thioxanthene in acetonitrile gave thianthrene and dark reddish thioxanthylium ion instead of thioxanthene cation radical. Addition of aromatic nucleophiles such as anisole, aniline, N,N-diethylaniline, catechol, ethylbenzene, to the above mixture yielded the corresponding thioxanthenes with substituent at 9 position. Reactions with dibenzo-18-crown-6-ether, diphenylmercury, and triphenylphosphine gave similar products. However, reactions with aromatics with electron-withdrawing group were either too slow or inert to such a reaction.

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References

  1. J. Amer. Chem. Soc. v.84 H. J. Shine;L. Piette
  2. J. Chem. Soc. E. A. Lucken
  3. Thesis, Univ. of Minnesota; Dissertation Abstr. v.22 W. C. Needler
  4. Organosulfur Chemistry The formation of cations and cation radicals from aromatic sulfides and sulfoxides M. J. Janssen(ed.)
  5. Proc. Coll. Natur. Sci. v.2 no.2 K. Kim
  6. STF-77-38 K. Kim;N. C. Jeong
  7. J. Amer. Chem. Soc. v.91 H. J. Shine;Y. Murata
  8. J. Org. Chem. v.34 Y. Murata;H. J. Shine
  9. J. Org. Chem. v.37 H. J. Shine;J. J. Silber;R. J. Bussey;T. Okuyama
  10. J. Amer. Chem. Soc. v.94 H. J. Shine;J. J. Silber
  11. Tetrahedron Lett. J. J. Shine;K. Kim
  12. J. Org. Chem. v.36 J. J. Silber;H. J. Shine
  13. J. Org. Chem. v.39 K. Kim;H. J. Shine
  14. Tetrahedron Lett. K. Kim;H. J. Shine
  15. J. Org. Chem. v.40 K. Kim;S. R. Mani;H. J. Shine
  16. Compt. Rend. v.255 B. Lamottee;A. Rassat;P. Servoz-gavin
  17. J. Org. Chem. v.30 H. J. Shine;E. Em Mach
  18. Acta, Chem. Scand. v.15 C. Lagercrantz
  19. Compt. Rend. v.255 D. Gagnaire;H. Lemaire;Q. Rassat;P. Servoz-Gavin
  20. Tetrahedron Lett. H. J. Shine;L. Hughes;D. R. Thompson
  21. J. Org. Chem. v.31 H. J. Shine;L. Hughes
  22. J. Amer. Chem. Soc. v.85 C. C. Price;M. Hori;T. Parasaran;M. Poek
  23. Handbook of Chemistry and Physics(55th ed.)
  24. Prog. Phys. Org. Chem. v.2 C. D. Richie;W. F. Sager
  25. J. Org. Chem. v.39 K. Kim;V. J. Hull;H. J. Shine
  26. J. Org. Chem. v.30 H. J. Shine;R. J. small
  27. J. Chim. Phys. v.61 S. Odiot;F. Tonnard
  28. Tetrahedron Lett. M. Tomita;S. Ueda;Y. Nakai;Y. Deguchi;H. Takaki
  29. J. Chim. Phys. v.61 J. P. Billon;G. Cauduis;J. Combrisson