Preparation and Electrooxidative SO-Extrusion of Halogenated 7-Thiabicyclo[2.2.1]heptene 7-Oxides†

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Thies Thiemann, M. Luisa Sa′ e Melo, Andre′ S. Campos Neves, Yuanqiang Li, Shuntaro Mataka, Masashi Tashiro, Uwe Geißler and David Walton


Abstract

Halogenated thiophenes have been cycloadded oxidatively to maleimides to give halogenated thiabicyclo[2.2.1]heptene S-oxides which have been subjected to an electrochemical extrusion of SO to give various halogeno-substituted phthalimides.


References

  1. K. Torssell, Acta Chem. Scand., Ser. B, 1976, 30, 353 Search PubMed.
  2. A. M. Naperstkow, J. B. Macaulay, M. J. Newlands and A. G. Gallis, Tetrahedron Lett., 1989, 30, 5077 CrossRef CAS.
  3. Y. Li, T. Thiemann, T. Sawada and M. Tashiro, J. Chem. Soc., Perkin Trans. 1, 1994, 2323 RSC.
  4. Y. Li, M. Matsuda, T. Thiemann, T. Sawada, S. Mataka and M. Tashiro, Synlett, 1996, 461 CrossRef CAS; Y. Li, T. Thiemann, T. Sawada, S. Mataka and M. Tashiro, J. Org. Chem., 1997, 62, 7926 CrossRef CAS.
  5. P. Pouzet, I. Erdelmeier, P. Ginderow, J. P. Mornon, D. M. Dansette and D. Mansuy, J. Chem. Soc., Chem. Commun., 1995, 473 RSC.
  6. C. Thiemann, T. Thiemann, Y. Li, T. Sawada, Y. Nagano and M. Tashiro, Bull. Chem. Soc. Jpn., 1994, 67, 1886 CAS.
  7. D. Scholz, Monatsh. Chem., 1981, 112, 241 CAS; D. G. Lee and N. Srinivasan, Sulfur Lett., 1982, 1, 1 Search PubMed.
  8. E. Fichter and F. Braun, Ber. Dtsch. Chem. Ges., 1910, 43, 3422.
  9. C. F. Bennett and D. W. Goheen, US Pat., 3 418 224, 1968(Chem. Abstr., 1969, 70, 43434g) Search PubMed.
  10. D. S. Houghton and A. A. Humffray, Electrochim. Acta, 1972, 17, 1421 CrossRef CAS; A. A. Humffray and D. S. Houghton, Electrochim. Acta, 1972, 17, 1435 CrossRef CAS.
  11. K. Uneyama and S. Torii, Tetrahedron Lett., 1971, 329 CrossRef CAS; S. Torii, K. Uneyama, K. Iida and K. Sasaki, Tetrahedron Lett., 1972, 4513 CrossRef.
  12. M. Eigen and K. Kustin, J. Am. Chem. Soc., 1962, 84, 1355 CrossRef CAS.
  13. M. Kimura, H. Kusai and Y. Sasaki, Electrochim. Acta, 1997, 42, 497 CrossRef CAS.
  14. L. R. Moraes, M. Weber and F. C. Nart, Electrochim. Acta, 1997, 42, 617 CrossRef.
  15. See D. Walton and V. S. Phull, Adv. Sonochem., 1996, 4, 205 Search PubMed.
  16. F. Marken, R. G. Compton, S. Savies, S. Bull, T. Thiemann, M. L. Sa e Melo, A. S. Campos Neves, J. Castillo, G. Jung and A. Fontana, J. Chem. Soc., Perkin Trans. 2, 1997, 2055 RSC and refs therein.
  17. D. S. Pratt and C. O. Young, J. Am. Chem. Soc., 1918, 40, 1415 CrossRef CAS.
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