Skip to main content
Log in

Molecular Structure of Thiophene 1,1-Dioxides, Thiophene S-oxides, and Their Derivatives. (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The results from X-ray diffraction investigations of compounds containing thiophene 1,1-dioxide and thiophene 1-monoxide fragments are reviewed and analyzed. Data on the structure of S-oxide derivatives of 2,3- and 2,5-dihydrothiophenes are discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. J. Nakayama and Y. Sugihara, Top. Curr. Chem., 205, 131 (1999).

    Google Scholar 

  2. G. Barbarella, L. Favaretto, M. Zambianchi, O. Pudova, C. Arbizzani, A. Bongini, and M. Masragostino, Adv. Mater. (Weinheim. Ger.), 10, 551 (1998).

    Google Scholar 

  3. G. Barbarella, L. Favaretto, G. Sotgiu, M. Zambianchi, V. Fattory, M. Cocchi, F. Cacialli, G. Gigli, and R. Cingolani, Adv. Mater. (Weinheim. Ger.), 11, 1375 (1999).

    Google Scholar 

  4. T. Yamamoto, I. Nurulla, H. Hayashi, and H. Koinuma, Synth. Met., 107, 137 (1999).

    Google Scholar 

  5. G. Barbarella, L. Favaretto, G. Sotgiu, M. Zambianchi, A. Bongini, C. Arbizzani, M. Masragostino, M. Anni, G. Gigli, and R. Cingolani, J. Am. Chem. Soc., 122, 11971 (2000).

    Google Scholar 

  6. L. G. Vorontsova, Zh. Strukt. Khim., 7, 240 (1966).

    Google Scholar 

  7. E. Lukevics, P. Arsenyan, S. Belyakov, J. Popelis, and O. Pudova, Organometallics, 18, 3187 (1999).

    Google Scholar 

  8. E. Lukevics, P. Arsenyan, S. Belyakov, J. Popelis, and O. Pudova, Tetrahedron Lett., 42, 2039 (2001).

    Google Scholar 

  9. N. Furukawa, H. Hoshiai, T. Shibutani, M. Higaki, F. Iwasaki, and H. Fujihara, Heterocycles, 34, 1085 (1992).

    Google Scholar 

  10. E. Lukevics, P. Arsenyan, S. Belyakov, J. Popelis, and O. Pudova, Organometallics, 20, 2487 (2001).

    Google Scholar 

  11. P. Pouzet, I. Erdelmeier, D. Ginderow, J.-P. Mornon, P. M. Dansette, and D. Mansuy, J. Heterocycl. Chem., 34, 1567 (1997).

    Google Scholar 

  12. G. Barbarella, L. Favaretto, G. Sotgiu, M. Zambianchi, L. Antolini, O. Pudova, and A. Bongini, J. Org. Chem., 63, 5497 (1998).

    Google Scholar 

  13. G. Douglas, C. S. Frampton, and K. W. Muir, Acta Crystallogr., C49, 1197 (1993).

    Google Scholar 

  14. J. L. M. Dillen, O. Meth-Cohn, C. Moore, and P. H. van Rooyen, Tetrahedron, 44, 3127 (1988).

    Google Scholar 

  15. W. Krebs, E. Franken, M. Müller, H. Colberg, W. Cholcha, J. Wilken, J. Ohrenberg, R. Albrecht, and E. Weiss, Tetrahedron Lett., 33, 5947 (1992).

    Google Scholar 

  16. E. Tedesco, B. M. Kariuki, K. D. M. Harris, R. L. Johnston, O. Pudova, G. Barbarella, E. A. Marseglia, G. Gigli, and R. Cingolani, J. Solid State Chem., 161, 121 (2001).

    Google Scholar 

  17. L. Antolini, E. Tedesco, G. Barbarella, L. Favaretto, G. Sotgiu, M. Zambianchi, D. Casarini, G. Gigli, and R. Cingolani, J. Am. Chem. Soc., 122, 9006 (2000).

    Google Scholar 

  18. J. Nakayama, Y. Sano, Y. Sugihara, and A. Ishii, Tetrahedron Lett., 40, 3785 (1999).

    Google Scholar 

  19. R. Albrecht and E. Weiss, J. Organomet. Chem., 399, 163 (1990).

    Google Scholar 

  20. K. Hoffmann and E. Weiss, J. Organomet. Chem., 128, 389 (1977).

    Google Scholar 

  21. R. Albrecht and E. Weiss, J. Organomet. Chem., 413, 355 (1991).

    Google Scholar 

  22. F. Meier-Brocks and E. Weiss, J. Organomet. Chem., 453, 33 (1993).

    Google Scholar 

  23. P. Pouzet, I. Erdelmeier, D. Ginderow, J.-P. Mornon, P. Dansette, and D. Mansuy, J. Chem. Soc. Chem. Commun., 473 (1995).

  24. J. A. Hashmall, V. Horak, L. E. Khoo, C. O. Quicksall, and M. K. Sun, J. Am. Chem. Soc., 103, 289 (1981).

    Google Scholar 

  25. I. Rozas, J. Phys. Org. Chem., 5, 74 (1992).

    Google Scholar 

  26. B. Jiang and T. Don Tilley, J. Am. Chem. Soc., 121, 9744 (1999).

    Google Scholar 

  27. N. Furukawa, S.-Z. Zhang, E. Horn, O. Takahashi, and S. Sato, Heterocycles, 47, 793 (1998).

    Google Scholar 

  28. J. Nakayama, T. Yu, Y. Sugihara, and A. Ishii, Chem. Lett., 499 (1997).

  29. S.-Z. Zhang, S. Sato, E. Horn, and N. Furukawa, Heterocycles, 48, 227 (1998).

    Google Scholar 

  30. E. Skaugset, T. B. Rauchfuss, and C. L. Stern, J. Am. Chem. Soc., 112, 2432 (1990).

    Google Scholar 

  31. M. S. El Amoudi El Faghi, P. Geneste, J. L. Olive, A. Dubourg, J. Rambaud, and J.-P. Declercq, Acta crystallogr., C43, 2421 (1987).

    Google Scholar 

  32. M. S. El Amoudi El Faghi, P. Geneste, J. L. Olive, J. Rambaud, and J.-P. Declercq, Acta crystallogr., C44, 498 (1988). 644

    Google Scholar 

  33. R. P. Gajewski, J. L. Jackson, N. D. Jones, J. K. Swartzendruber, and J. B. Deeter, J. Org. Chem., 54, 3311 (1989).

    Google Scholar 

  34. V. E. Udre, E. Ya. Lukevics, A. A. Kemme, and Ya. Ya. Bleidelis, Khim. Geterotsikl. Soedin., 320 (1980).

  35. A. A. Kemme, M. F. Bundule, Ya. Ya. Bleidelis, V. E. Udre, and E. Lukevics, Zh. Strukt. Khim., 21, No. 6, 123 (1980).

    Google Scholar 

  36. R. Guilard and Y. Dusausoy, J. Organomet. Chem., 77, 393 (1974).

    Google Scholar 

  37. H.-H. Chen, J. A. May, and V. M. Lynch, J. Heterocycl. Chem., 36, 249 (1999).

    Google Scholar 

  38. L. R. Kronfeld and R. L. Sass, Acta crystallogr., B24, 981 (1968).

    Google Scholar 

  39. I. Goldberg and U. Shmueli, Acta crystallogr., B27, 2173 (1971).

    Google Scholar 

  40. V. M. Polosin, A. A. Astakhov, I. A. Tafeenko, and A. V. Ivashchenko, Zh. Obshch. Khim., 62, 367 (1992).

    Google Scholar 

  41. D. R. Boyd, N. D. Sharma, S. A. Haughey, J. F. Malone, B. T. McMurray, G. N. Sheldrake, C. C. R. Alien, and H. Dalton, J. Chem. Soc. Chem. Commun., 2363 (1996).

  42. G. G. Rode, T. E. Bezmenova, M. Yu. Antipin, Yu. T. Struchkov, I. A. Litvinov, A. I. Yanovskii and G. V. Klimusheva, Zh. Strukt. Khim., 25, No. 4, 160 (1984).

    Google Scholar 

  43. G. V. Klimusheva. T. E. Bezmenova, G. M. Soroka, and G. G. Rode, Tetrahedron, 36, 1667 (1980).

    Google Scholar 

  44. G. G. Rode, T. E. Bezmenova, M. Yu. Antipin, Yu. T. Struchkov, and G. V. Klimusheva, Zh. Strukt. Khim., 25, 158 (1984).

    Google Scholar 

  45. G. G. Rode, D. S. Yufit, T. E. Bezmenova, and G. V. Klimusheva, Ukr. Khim. Zh., 53, 751 (1987).

    Google Scholar 

  46. G. G. Rode, D. S. Yufit, Yu. T. Struchkov, A. N. Chernego, T. E. Bezmenova, and G. V. Klimusheva, Ukr. Khim. Zh., 53, 1309 (1987).

    Google Scholar 

  47. H. J. Kuhn, R. Defoin, K. Gollnick, C. Kruger, Y.-H. Tsay, L.-K. Liu, and P. Betz, Tetrahedron, 45, 1667 (1989).

    Google Scholar 

  48. B. R. Dent and G. J. Geinsford, Aust. J. Chem., 42, 1307 (1989).

    Google Scholar 

  49. V. M. Berestovitskaya, M. F. Bundule, Ya. Ya. Bleidelis, and I. E. Efremova, Zh. Obshch. Khim., 54, 1182 (1984).

    Google Scholar 

  50. E. Lukevics, P. Arsenyan, S. Belyakov, J. Popelis, and O. Pudova, Eur. J. Org. Chem., 3139 (2000).

  51. S. Gronowitz, G. Nikitidis, A. Hallberg, and C. Stalhandske, Acta Chem. Scand., B41, 297 (1987).

    Google Scholar 

  52. S. Gronowitz, G. Nikitidis, A. Hallberg, and C. Stalhandske, Acta Chem. Scand., 45, 636 (1991).

    Google Scholar 

  53. S.-K. Yeo, M. Shiro, and K. Kanematsu, J. Org. Chem., 59, 1621 (1994).

    Google Scholar 

  54. G. A. Jefferey, Acta Crystallogr., 4, 58 (1951).

    Google Scholar 

  55. G. G. Rode, T. E. Bezmenova, M. Yu. Antipin, Yu. T. Struchkov, G. V. Klimusheva, and A. P. Polishchuk, Zh. Strukt. Khim., 25, No. 4, 159 (1984).

    Google Scholar 

  56. T. Fernandez, D. Suarez, J. A. Sordo, F. Monnat, E. Roversi, A. E. de Castro, K. Schenk, and P. Vogel, J. Org. Chem., 63, 9490 (1998).

    Google Scholar 

  57. A. Laila and N. S. Isaacs, Monatsh. Chem., 116, 933 (1985).

    Google Scholar 

  58. V. M. Berestovitskaya, M. F. Bundule, Ya. Ya. Bleidelis, and I. E. Efremova, Zh. Obshch. Khim., 56, 375 (1986).

    Google Scholar 

  59. G. Hieber, M. Hanack, K. Wurst, and J. Strähle, Chem. Ber., 124, 1597 (1991).

    Google Scholar 

  60. V. V. Tkachev, L. O. Atovmyan, V. M. Berestovitskaya, and I. E. Efremova, Zh. Strukt. Khim., 33, No. 5, 103 (1992).

    Google Scholar 

  61. J. H. Eekhof, H. Hogeveen, and R. M. Kellogg, J. Organomet. Chem., 161, 361 (1978).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lukevics, E., Arsenyan, P., Belyakov, S. et al. Molecular Structure of Thiophene 1,1-Dioxides, Thiophene S-oxides, and Their Derivatives. (Review). Chemistry of Heterocyclic Compounds 38, 632–645 (2002). https://doi.org/10.1023/A:1019904916596

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1019904916596

Navigation