Bulletin of the Korean Chemical Society

  • 제8권5호
  • /
  • Pages.380-384
  • /
  • 1987
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

Reaction of Methylenethioxanthene with Thiyl Radical: Formation of A Vinyl Sulfide

  • 발행 : 1987.10.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Reactions of methylenethioxanthene (3) with n-propanethiol in the presence of di-t-butyl peroxide(DTBP) afforded preferentially propyl 9-thioxanthenylidenemethyl sulfide(8) rather than propyl 9-thioxanthenylmethyl sulfide(9) regardless of the concentration of n-propanethiol. On the other hand reactions of 3 with a low concentration of n-propanethiol in the presence of dibenzoyl peroxide(DBPO) gave 8, 1,2-bisthioxanthenylidene ethane(11), and thioxanthenylidenemethyl benzoate(12) but only 8 was formed at high concentration of the thiol. The formations of these products were rationallized by an electron transfer mechanism.

키워드

참고문헌

  1. Bull. Korean Chem. Soc. v.2 D. Shin;K. Kim
  2. Bull. Korean Chem. Soc. v.3 S. Kim;K. Kim
  3. J. Org. Chem. v.18 H. H. Szmant;M. J. Segedi;J. Dudek
  4. J. Org. Chem. v.31 H. J. Shine;L. Hughes
  5. J. Am. Chem. Soc. v.85 C. C. Price;M. Hori;T. Parasan;M. B. Polk
  6. J. Am. Chem. Soc. v.88 G. A. Olah;N. Friedman
  7. J. Am. Chem. Soc. v.96 W. H. Richardson;F. C. Montgomery;M. B. Yelvington;H. E. O'Neal
  8. J. Am. Chem. Soc. v.97 W. H. Richardson;F. C. Montgomery;P. Slusser;M. B. Yelvington
  9. Free Radicals v.II P. I. Abell;J. K. Kochi(ed.)
  10. Free radicals in solution C. Walling
  11. Chem. Rev. v.27 F. R. Mayo;C. Walling
  12. Methods in Free Radical Chemistry v.II R. M. Kellog;E. S. Huyser(ed.)
  13. J. Am. Chem. Soc. v.93 T. Kawamura;M. Ushio;T. Fujimoto;T. Yonezawa
  14. Tetrahedron Letts. H. Seott;G. A. Miller;M. M. Labes
  15. J. Am. Chem. Soc. v.91 W. Bracke;W. J. Cheng;J. M. Pearson;M. Szwarc
  16. J. Org. Chem. v.34 H-D. Becker
  17. J. Chem. Soc., Perkin II K. Takeuchi;O. Murai;S. Matsui;T. Inoue;T. Kitagawa;K. Okamoto
  18. J Chem. Soc., Perkin I C-M. Camaggi;R. Leardini;A. Tundo;M. Tiecco
  19. J. Am. Chem. Soc. v.84 J. K. Kochi
  20. J. Chem. Soc. B G.R. Chalfont;M.J. Perkins
  21. Organometallic Mechanisms and Catalysis J.K. Kochi
  22. Bull. Chem. Soc., Jap. v.35 T. Yonezawa;H. Kato;H. Saito;K. Fukui
  23. Bull. Chem. Soc., Jap. v.44 K. Ohkubo;M. Okada
  24. J. Phys. Chem. v.72 T. Shida
  25. J. Am. Chem. Soc. v.96 W. A. Nugent;F. Bertini;J. K. Kochi
  26. J. Chem. Soc., Perkin Trans. v.1 S. Uemura;T. Ikeda;M. Okano
  27. Collect. Czeck, Chem. Commun. v.44 M. Hajek;P. Silhavy;J. Malek
  28. J. Am. Chem. Soc. v.84 J. K. Kochi
  29. Organic Reaction Mechanisms D. J. Cowley;A. C. Knipe(ed.);W. E. Watts(ed.)
  30. Free-radical Chemistry D. C. Nonhebel;J. C. Walton