Silicon-Sulfur

  • William P. Weber
Part of the Reactivity and Structure Concepts in Organic Chemistry book series (REACTIVITY, volume 14)

Abstract

Silicon-sulfur and selenium compounds have proved to be valuable synthetic reagents [1]. The preparation of both vinyl thio ethers [2, 3] and vinyl sulfinyl ethers [4] by the Peterson reaction has been discussed [2], as well as reductions of sulfoxides by silyl sulfide [5] and silyl selenide [6] reagents (20.6).

Keywords

Sulfide Aldehyde Phenyl Ketone Thiol 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. For a review of silicon-sulfur Chemistry see: Abel, E.W. Armitage, D.A.: Adv. Organometal. Chem. 5, 2 (1967)Google Scholar
  2. 2.
    Peterson, D.J.: J. Org. Chem. 33, 780 (1968)CrossRefGoogle Scholar
  3. 3.
    Carey, F.A., Court, A.S.: J. Org. Chem. 37, 939 (1972)CrossRefGoogle Scholar
  4. 4.
    Carey, F.A., Hernandez, O.: J. Org. Chem. 38, 2670 (1973)CrossRefGoogle Scholar
  5. 5.
    Soysa, H.S.D., Weber, W.P.: Tetrahedron Lett. 235 (1978)Google Scholar
  6. 6.
    Detty, M.R.: J. Org. Chem. 44, 4528 (1979)CrossRefGoogle Scholar
  7. 7.
    Walsh, R.: Accts. of Chem. Res. 14, 246 (1981)CrossRefGoogle Scholar
  8. 8.
    Schmeisser, M., Muller, H.: On the basis of equilibration studies, Si-S and C—S single bonds appear to be approximately equal strength: Angew. Chem, 69, 781 (1957)Google Scholar
  9. 9.
    Abel, E.W., Walker, D.J.: J. Chem. Soc. A, 2338 (1968)Google Scholar
  10. 10.
    Rokach, J., Girard, Y., Guidon, Y., Atkinson, J.G., Larue, M., Young, R.N., Mas-son, P., Holme, G.: Tetrahedron Lett. 1485 (1980)Google Scholar
  11. 11.
    Hanessian, S., Guindon, Y.: Tetrahedron Lett. 2305 (1980)Google Scholar
  12. 12.
    Miyoshi, N., Kondo, K., Murai, S., Sonoda, N.: Chem. Lett. 909 (1979)Google Scholar
  13. 13.
    Detty, M.R.: Tetrahedron Lett. 5087 (1978)Google Scholar
  14. 14.
    Abel, E.W., Walker, D.J., Wingfield, N.J.: J. Chem. Soc. A, 1814 (1968)Google Scholar
  15. 15.
    Itoh, K., Matsuzaki, K., Ishii, Y.: J. Chem. Soc. C, 2709 (1968)Google Scholar
  16. 16.
    Ojima, I., Nagai, Y.: J. Organometal. Chem. 57, C42 (1973)CrossRefGoogle Scholar
  17. 17.
    Evans, D.A., Grimm, K.G., Truesdale, L.K.: J. Am. Chem. Soc. 97, 3229 (1975)CrossRefGoogle Scholar
  18. 18.
    Evans, D.A., Truesdale, L.K., Grimm, K.G., Nesbitt, S.L.: J. Am. Chem. Soc. 99, 5009 (1977)CrossRefGoogle Scholar
  19. 19.
    Chan, T.H., Ong, B.S.: Tetrahedron Lett. 319 (1976)Google Scholar
  20. 20.
    Glass, R.S.: Syn. Comm. 6, 47 (1976)CrossRefGoogle Scholar
  21. 21.
    Ong, B.S., Chan, T.H.: Syn. Commun. 7, 283 (1977)CrossRefGoogle Scholar
  22. 22.
    Dumont, W., Krief, A.: Angew. Chem. Int. Ed. 16, 540 (1977)CrossRefGoogle Scholar
  23. 23.
    Liotta, D., Paty, P.B., Johnston, J., Zima, G.: Tetrahedron Lett. 5091 (1978)Google Scholar
  24. 24.
    Itoh, K., Matsuzaki, K., Ishii, Y.: J. Chem. Soc. C, 2709 (1968)Google Scholar
  25. 25.
    Mukaiyama, T., Takeda, T., Atsumi, K.: Chem. Lett. 187 (1974)Google Scholar
  26. 26.
    Breslow, R., Pandey, P.S.: J. Org. Chem. 45, 740 (1980)CrossRefGoogle Scholar
  27. 27.
    Miyoshi, N., Ishii, H., Murai, S., Sonoda, N.: Chem. Lett. 873 (1979)Google Scholar
  28. 28.
    Ricci, A., Danieli, R., Pirazzini, G.: J.C.S. Perkin 1, 1069 (1977)CrossRefGoogle Scholar
  29. 29.
    Mukaiyama, T., Takeda, T., Atsumi, K.: Chem. Lett. 1013 (1974)Google Scholar
  30. 30.
    Kuwajima, I., Hoshino, S., Tanaka, T., Shimizu, M.: Tetrahedron Lett. 3209 (1980)Google Scholar
  31. 31.
    Dumont, W., Krief, A.: Angew. Chem. Int. Ed. 15, 161 (1976)CrossRefGoogle Scholar
  32. 32.
    Brook, A.G., Anderson, D.G.: Can. J. Chem. 46, 2115 (1968)CrossRefGoogle Scholar
  33. 33.
    Vedejs, E., Mullins, M.: Tetrahedron Lett. 2017 (1975)Google Scholar
  34. 34.
    Cooper, G.D.: J. Am. Chem. Soc. 76, 3713 (1954)CrossRefGoogle Scholar
  35. 35.
    Corey, E.J., Seebach, D.: J. Org. Chem. 31, 4097 (1966)CrossRefGoogle Scholar
  36. 36.
    Kocienski, P.J.: Tetrahedron Lett. 1559 (1980)Google Scholar
  37. 37.
    Ager, D.J., Cookson, R.C.: Tetrahedron Lett. 1677 (1980)Google Scholar
  38. 38.
    Ager, D.J.: Tetrahedron Lett. 4759 (1980)Google Scholar
  39. 39.
    Ager, D.J.: Tetrahedron Lett. 587 (1981)Google Scholar
  40. 40.
    Harirchian, B., Magnus, P.: J. Chem. Soc. Chem. Commun. 522 (1977)Google Scholar
  41. 41.
    Cookson, R.C., Parsons, P.J.: J. Chem. Soc. Chem. Commun. 990 (1976)Google Scholar
  42. 42.
    Sachdev, K., Sachdev, H.S.: Tetrahedron Lett. 4223 (1976)Google Scholar
  43. 43.
    Reich, H.J., Shan, S.K.: J. Org. Chem. 42, 1773 (1977)CrossRefGoogle Scholar
  44. 44.
    Reich, H.J.: J. Org. Chem. 40, 2570 (1975)CrossRefGoogle Scholar
  45. 45.
    Cutting, I., Parsons, P.J.: Tetrahedron Lett. 2021 (1981)Google Scholar
  46. 46.
    Kocienski, P.J.: J. Chem. Soc. Chem. Commun. 1096 (1980)Google Scholar
  47. 47.
    Harpp, D.N., Friedlander, B.T., Larsen, C., Steliou, K., Stockton, A.: J. Org. Chem. 43, 3481 (1978)CrossRefGoogle Scholar
  48. 48.
    Wieber, M., Schmidt, M.: J. Organometal. Chem. I, 336 (1964)CrossRefGoogle Scholar
  49. 49.
    Yamazaki, N., Nakahama, S., Yamaguchi, K., Yamaguchi, T.: Chem. Lett. 1355 (1980)Google Scholar
  50. 50.
    Wieber, M., Schmidt, H.: Z. Naturf. 18, 846 (1963)Google Scholar
  51. 51.
    Shanzer, A., Schwartz, E.: Tetrahedron Lett. 5019 (1979)Google Scholar
  52. 52.
    Derkach, N.Y., Tishchenko, N.P.: Zh. Org. Khim. 13, 100 (1977)Google Scholar
  53. 53.
    Dean, F.M., Goodchild, J., Hill, A.W.: J. Chem. Soc. C, 2192 (1969)Google Scholar
  54. 54.
    For a review see Klebe, J.F.: Adv. Org. Chem. 8, 97–178 (1972)Google Scholar
  55. 55.
    Kuwajima, I., Mori, A., Kato, M.: Bull. Chem. Soc. Japan, 53, 2634, (1980)CrossRefGoogle Scholar
  56. 56.
    Larsen, C., Steliou, K., Harpp, D.N.: J. Org. Chem. 43, 337 (1978)CrossRefGoogle Scholar
  57. 57.
    Harpp, D.N., Friedlander, B.T., Mullins D., Vines, S.M.: Tetrahedron Lett. 963 (1977)Google Scholar
  58. 58.
    Harpp, D.N., Steliou, K., Chan, T.H.: J. Am. Chem. Soc. 100, 1222, (1978)CrossRefGoogle Scholar
  59. 59.
    Walter, W., Lüke, H.W., Voss, J.: Liebigs. Ann. Chem. 1808 (1975)Google Scholar
  60. 60.
    Walter, W., Lüke, H.W.: Angew. Chem. Int. Ed. 14, 427 (1975)Google Scholar
  61. 61.
    Walter, W., Lüke, H.W.: Angew. Chem. Int. Ed. 16, 535 (1977)CrossRefGoogle Scholar
  62. 62.
    Hootan, K.A., Allred, A.L.: Inorg. Chem. 4, 671 (1965)CrossRefGoogle Scholar
  63. 63.
    Harris, S.J., Walton, D.R.M.: J. Chem. Soc. Chem. Commun. 1008 (1976)Google Scholar
  64. 64.
    Miyoshi, N., Ishii, H., Kondo, K., Murai, K., Sonoda, N.: Synthesis, 300 (1979)Google Scholar
  65. 65.
    Liotta, D., Markiewicz, W., Santiesteban, H.: Tetrahedron Lett. 4365 (1977)Google Scholar
  66. 66.
    Praefcke, K., Weichsel, C.: Synthesis, 216 (1980)Google Scholar
  67. 67.
    Louis, E., Urry, G.: J. Inorg. Chem. 7, 1253 (1968)CrossRefGoogle Scholar
  68. 68.
    Glass, R.S.: J. Organometal. Chem. 61, 83 (1973)CrossRefGoogle Scholar
  69. 69.
    Harpp, D.N., Steliou, K.: Synthesis, 721 (1976)Google Scholar
  70. 70.
    Derkach, N.Y., Pasmurtseva, N.A., Levchenko, E.S.: Zh. Org. Khim. 7, 1543 (1971)Google Scholar
  71. 71.
    Ojima, I., Nihonyanagi, M., Nagai, Y.: J. Organometal. Chem. 50, C26 (1973)CrossRefGoogle Scholar
  72. 72.
    Sommer, L.H., Citron, J.D.: J. Org. Chem. 32, 2470 (1967)CrossRefGoogle Scholar
  73. 73.
    Kuwajima, I., Abe, T.: Bull. Chem. Soc. Japan, 51, 2183 (1978)CrossRefGoogle Scholar
  74. 74.
    Hayashi, T., Midorikawa, H.: Tetrahedron Lett. 2461 (1973)Google Scholar
  75. 75.
    Abel, E.W., Armitage, D.A., Bush, R.P.: J. Chem. Soc. 2455 (1964)Google Scholar
  76. 76.
    Rimpler, M.: Chem. Ber. 99, 1528 (1966)CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1983

Authors and Affiliations

  • William P. Weber
    • 1
  1. 1.Department of ChemistryUniversity of Southern CaliforniaUniversity Park, Los AngelesUSA

Personalised recommendations