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Dihydrothiophenes. Synthesis and properties (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The literature data on the methods of synthesis and properties of 2,3-dihydrothiophene and 2,5-dihydrothiophene have been correlated for the first time.

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References

  1. W. Steinkopf, Die Chemie des Thiophens, T. Steinkopf, Leipzig (1941).

    Google Scholar 

  2. F. Blick in: R. E. Elderfield (ed.), Heterocyclic Compounds: Chemistry of Thiophenes, Vol. 1, Wiley, New York (1950), p. 165.

    Google Scholar 

  3. H. D. Hartough, Thiophene and Its Derivatives, Interscience, New York (1952).

    Google Scholar 

  4. O. Meth-Kohn in: P. G. Sammes (ed.), Comprehensive Organic Chemistry: Heterocyclic Compounds, Vol. 4, Pergamon Press, Oxford (1979), p. 229.

    Google Scholar 

  5. A. R. Katritzky and C. A. Rees (eds.), Comprehensive Heterocyclic Chemistry, Vol. 4, Pergamon Press, Oxford (1984), p. 713.

    Google Scholar 

  6. S. Gronowitz (ed.), Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Vol. 44, Part 1, Wiley, New York (1985).

    Google Scholar 

  7. L. I. Belen'kii in: L. N. Belenskii (ed.), Chemistry of Organic Sulfur Compounds. General Problems [in Russian], Khimiya, Moscow (1988), p. 191.

    Google Scholar 

  8. Ya. M. Slobodin, Zh. Obshch. Khim.,8, 714 (1938).

    CAS  Google Scholar 

  9. S. F. Birch and D. T. McAllan, Nature,165, 899 (1950).

    CAS  Google Scholar 

  10. R. H. Everhardus, R. Grafing, and L. Brandsma, Rec. Trav. Chim.,96, 153 (1976).

    Google Scholar 

  11. J. E. O'Gara, J. D. Portmess, and K. B. Wagener, Macromolecules,26, 2837 (1993); Chem. Abs.,118, 234601 (1993).

    Article  Google Scholar 

  12. J.-L. Couturier, K. Tanaka, M. Leconte, J.-M. Basset, and J. Ollivier, Angew. Chem. Int. Ed. Engl.,32, 112 (1993).

    Article  Google Scholar 

  13. L.-F. Liao, P.-W. Tseng, C.-H. Chou, W.-C. Chou, and J.-M. Fang, Heterocycles,41, 1967 (1995); Chem. Abs.,124, 55075 (1996).

    CAS  Google Scholar 

  14. C. Dupuy and J.-M. Surzur, Bull. Soc. Chim. France, Nos. 7-8, 353 (1980).

    Google Scholar 

  15. B. A. Trofimov, S. V. Amosova, N. K. Gusarova, and G. K. Musori, Tetrahedron,38, 713 (1982).

    Article  CAS  Google Scholar 

  16. L. M. Petrova, A. A. Freger, and E. A. Viktorova, Vestn. Mosk. Univ., Khim.,15, 498 (1974).

    CAS  Google Scholar 

  17. G. Vermeersch, J. Marko, N. Febvay-Garot, S. Caplain, A. Couture, and A. Lablache-Combier, Tetrahedron,34, 2453 (1978).

    CAS  Google Scholar 

  18. P. A. Delaney and R. A. Johnstone, J. Chem. Soc. Perkin Trans.,1, 1861 (1986).

    Google Scholar 

  19. G. Lange, M. E. Savard, T. Viswanatha, and G. I. Dmitrienko, Tetrahedron Lett.,26, 1791 (1985).

    CAS  Google Scholar 

  20. G. Sosnovsky, US Patent 3144438; Chem. Abs.,61, 13283 (1964).

    Google Scholar 

  21. G. E. Wilson and R. Albert, J. Org. Chem.,38, 2156 (1973).

    CAS  Google Scholar 

  22. G. Sosnovsky, J. Org. Chem.,26, 281 (1961).

    CAS  Google Scholar 

  23. G. Sosnovsky, Tetrahedron,18, 903 (1962).

    CAS  Google Scholar 

  24. C. Berglund and S.-O. Lawesson, Ark. Kemi,20, 225 (1963).

    CAS  Google Scholar 

  25. C. Berglund and S.-O. Lawesson, Acta Chem. Scand.,16, 773 (1962).

    CAS  Google Scholar 

  26. D. L. Schmidt, J. P. Heeschen, T. C. Klinger, and L. P. McCarty, J. Org. Chem.,50, 2840 (1985).

    Article  CAS  Google Scholar 

  27. N. N. Sauer, R. J. Angelici, Y. C. Huang, and W. S. Trahanovsky, J. Org. Chem.,51, 113 (1986).

    Article  CAS  Google Scholar 

  28. J. M. Cox and L. N. Owen, J. Chem. Soc. (C), 1130 (1967).

  29. M. A. Gianturco, P. Friedel, and V. Flanagan, Tetrahedron Lett., No. 23, 1847 (1965).

    Google Scholar 

  30. P. Y. Johnson, E. Koza, and R. E. Kohrman, J. Org. Chem.,38, 2967 (1973).

    CAS  Google Scholar 

  31. R. Krug and D. E. Baswell, J. Heterocycl. Chem.,4, 309 (1967).

    CAS  Google Scholar 

  32. J. N. Gardner, S. Kaiser, A. Krubiner, and H. Lucas, Can. J. Chem.,51, 1419 (1973).

    CAS  Google Scholar 

  33. J. N. Gardner, US Patent 3819652; Ref. Zh. Khim.,2N, 148P (1976).

  34. T. Fujisawa, M. Kakutani, and K. Hata, Japanese Patent 75-117768; Chem. Abs.,84, 59173 (1976).

    Google Scholar 

  35. S. F. Birch and D. T. McAllan, J. Chem. Soc., No. 10, 2556 (1951).

    Google Scholar 

  36. J. V. Davies and S. Sunner, Acta Chem. Scand.,16, 1870 (1962).

    CAS  Google Scholar 

  37. P. K. Korver, P. J. Van der Haak, H. Steinberg, and T. J. Boer, Rec. Trav. Chim.,84, 129 (1965).

    CAS  Google Scholar 

  38. R. C. Krug and S. Tocker, J. Org. Chem.,20, 1 (1955).

    Article  CAS  Google Scholar 

  39. Yu. I. Lyakhovetskii, F. M. Latypova, N. K. Lyapina, and Z. N. Parnes, Zh. Org. Khim.,28, 1275 (1992).

    CAS  Google Scholar 

  40. D. A. Lesch, J. W. Richardson, R. A. Jacobson, and R. J. Angelici, J. Am. Chem. Soc.,106, 2901 (1984).

    Article  CAS  Google Scholar 

  41. C. Bianchini, A. Meli, M. Peruzzini, F. Vizza, V. Herrera, and R. A. Sanchez-Delgado, Organometallics,13, 721 (1994).

    CAS  Google Scholar 

  42. J. W. Lown, R. R. Koganty, and A. V. Joshua, J. Org. Chem.,47, 2027 (1982).

    CAS  Google Scholar 

  43. J. M. McIntosh and M. A. Siddiqui, Can. J. Chem.,61, 1872 (1983).

    CAS  Google Scholar 

  44. T. Ueda and T. Shimanouchi, J. Chem. Phys.,47, 5018 (1967).

    CAS  Google Scholar 

  45. R. L. Rosas, C. Cooper, and J. Laane, J. Phys. Chem.,94, 1830 (1990).

    Article  CAS  Google Scholar 

  46. W. H. Green and A. B. Harvey, Spectrochim. Acta A,25, 723 (1969).

    CAS  Google Scholar 

  47. W. H. Green and A. B. Harvey, J. Chem. Phys.,49, 177 (1968).

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  49. M. Prochazka and M. Palacek, Collect. Czech. Chem. Commun.,32, 3149 (1967).

    CAS  Google Scholar 

  50. J. R. Durig, R. O. Carter, and L. A. Carreira, J. Chem. Phys.,59, 2249 (1973).

    CAS  Google Scholar 

  51. J. R. Durig, T. S. Little, and Y. S. Li, J. Chem. Phys.,76, 3849 (1982).

    CAS  Google Scholar 

  52. J. C. Lopez, E. A. Degli, D. G. Lister, R. Cervellati, J. L. Alonso, and L. Forlani, J. Mol. Struct.,42, 97 (1986); Chem. Abs.,104, 195860 (1986).

    Google Scholar 

  53. R. J. Abraham, K. Perry, and W. A. Thomas, J. Chem. Soc. (B), No. 3, 446 (1971).

    Google Scholar 

  54. A. Xicluna and J. E. Robert, Rev. Rom. Chim.,31, 143 (1986).

    CAS  Google Scholar 

  55. L. Bateman and F. W. Shipley, J. Chem. Soc., No. 8, 2888 (1958).

    Google Scholar 

  56. L. A. Cohen and A. Steele, J. Org. Chem.,31, 2333 (1966).

    CAS  Google Scholar 

  57. S. F. Birch and D. T. McAllan, J. Chem. Soc., No. 1, 233 (1952).

    Google Scholar 

  58. H. C. Brown, J. V. N. Vara Prasad, and C.-E. Zee, J. Org. Chem.,50, 1582 (1985).

    CAS  Google Scholar 

  59. H. C. Brown and J. V. N. Nara Prasad, J. Am. Chem. Soc.,108, 2049 (1986).

    CAS  Google Scholar 

  60. H. C. Brown, P. V. Ramachandran, and J. V. N. Vara Prasad, J. Org. Chem.,50, 5583 (1985).

    CAS  Google Scholar 

  61. S. M. Liebowitz and H. J. Johnson, Synth. Commun.,16, 1255 (1986).

    CAS  Google Scholar 

  62. S. Fries, K. Gollnick, and R. Huisgen, Angew. Chem.,92, 848 (1980).

    CAS  Google Scholar 

  63. S. Lee-Ruff and Y.-S. Chung, J. Heterocycl. Chem.,23, 1551 (1986).

    CAS  Google Scholar 

  64. L. Fisera, J. Kovac, J. Patus, and P. Mesco, Chem. Zvesti,37, 819 (1983).

    CAS  Google Scholar 

  65. P. Caramella, T. Bandiera, P. Grunanger, and F. M. Albini, Tetrahedron,40, 441 (1984).

    Article  CAS  Google Scholar 

  66. K. Gollnick, S. Fries, and R. Huisgen, Angew. Chem.,92, 848 (1980).

    CAS  Google Scholar 

  67. F. Thalhammer, U. Wallfahrer, and J. Sauer, Tetrahedron Lett.,31, 6851 (1990).

    Article  CAS  Google Scholar 

  68. A. L. Cardon and E. J. Goethals, Macromol. Chem.,175, 3147 (1974).

    CAS  Google Scholar 

  69. L. A. Paquette, B. M. Branan, D. Friedrich, S. D. Edmondson, and R. D. Rogers, J. Am. Chem. Soc.,116, 506 (1994).

    CAS  Google Scholar 

  70. L. A. Paquette, U. Dullweber, and B. M. Branan, Heterocycles,37, 187 (1994); Chem. Abs.,120, 269985 (1994).

    CAS  Google Scholar 

  71. T. Tsujikawa and M. Hayashi, Chem. Pharm. Bull.,25, 3147 (1977).

    CAS  Google Scholar 

  72. N. N. Sauer, E. J. Markel, G. L. Schrader, and R. J. Angelici, J. Catal.,117, 295 (1989).

    Article  CAS  Google Scholar 

  73. N. N. Sauer and R. J. Angelici, Inorg. Chem.,26, 2160 (1987).

    Article  CAS  Google Scholar 

  74. M.-G. Choi, L. M. Daniels, and R. J. Angelici, Inorg. Chem.,30, 3647 (1991).

    CAS  Google Scholar 

  75. G. N. Glavee, L. M. Daniels, and R. J. Angelici, Organometallics,8, 1856 (1989).

    Article  CAS  Google Scholar 

  76. P. Desikan and C. H. Amberg, Can. J. Chem.,42, 843 (1964).

    CAS  Google Scholar 

  77. H. Kloosterziel, J. A. A. Van Drunen, and P. Galama, J. Chem. Soc., Chem. Commun., 885 (1969).

  78. A. C. Liu and C. M. Friend, J. Am. Chem. Soc.,113, 820 (1991).

    CAS  Google Scholar 

  79. H. Xu and C. M. Friend, J. Phys. Chem.,97, 3584 (1993).

    CAS  Google Scholar 

  80. E. J. Markel, G. L. Schrader, N. N. Sauer, and R. J. Angelici, J. Catal.,116, 11 (1989).

    Article  CAS  Google Scholar 

  81. N. N. Sauer, Energy Res. Abs.,12, 35322 (1987); Chem. Abs.,108, 114626 (1988).

    Google Scholar 

  82. J. W. Benson, G. L. Schrader, and R. J. Angelici, J. Mol. Catal. A,96, 283 (1995).

    CAS  Google Scholar 

  83. J. Gabay, S. Dietz, P. Beratis, and M. R. Du Bois, Organometallics,12, 3630 (1993).

    Article  CAS  Google Scholar 

  84. P. S. Skell, K. J. Klabunde, J. H. Plonka, J. S. Roberts, and D. L. Williams-Smith, J. Am. Chem. Soc.,95, 1547 (1973).

    CAS  Google Scholar 

  85. K. Friedrich and J. Rieser, Justus Liebigs Ann. Chem., 641 (1976).

  86. M. R. Bryce, J. N. Heaton, P. C. Tayler, and M. Anderson, J. Chem. Soc. Perkin Trans. 1, No. 14, 1935 (1994).

    Google Scholar 

  87. C. A. Willington, T. L. James, and A. C. Thomas, J. Chem. Soc. (A), 2897 (1969).

  88. Soda Aromatic Co., Ltd., Japanese Patent 58-74792; Chem. Abs.,99, 142924 (1983).

    Google Scholar 

  89. Fuji Photo Film Co., Ltd., Japanese Patent 82-22234; Chem. Abs.,97, 172415 (1982).

    Google Scholar 

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  1. M. -G. A. Shvekhgeimer
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A. N. Kosygin Moscow State Textile Academy, Moscow 117918, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1299–1324, October, 1998.

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Shvekhgeimer, M.G.A. Dihydrothiophenes. Synthesis and properties (review). Chem Heterocycl Compd 34, 1101–1122 (1998). https://doi.org/10.1007/BF02319487

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