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Part of the book series: Reactivity and Structure Concepts in Organic Chemistry ((REACTIVITY,volume 14))

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Abstract

In addition to ionic hydrogenations, dissolving metal reductions and hydrosilation reactions which we have previously considered, there are a number of reduction reactions which utilize organosilicon reagents. These have been divided into seven sections: 1) tin hydride mediated reductions, 2) reductions which utilize silyl radicals, 3) reductions with trichlorosilane (Cl3SiH)/tertiary amines, 4) reductions of phosphine oxides, 5) reductions of sulfoxides, 6) reductions of amine oxides, and 7) reductions of α-halo ketones. The organizing principle of the first three sections is the combination of reagents used or the reactive intermediates involved. The latter four sections are concerned with reductions of specific functional groups.

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References

  1. Kuivila, H.G., Advances in Organometallic Chem., 1, 47, New York: Academic Press 1964

    Google Scholar 

  2. Poller, R.C.: The Chemistry of Organotin Compounds, p. 105–107, New York: Academic Press, 1970

    Google Scholar 

  3. Hayashi, K., Iyoda, J., Shiihara, I.: J. Organometal. Chem. 10, 81 (1967)

    Article  CAS  Google Scholar 

  4. Bellegarde, B., Pereyre, M., Valade, J.: Bull. Soc. Chem. Fr. 3082 (1967)

    Google Scholar 

  5. Pereyre, M., Pijselman, J.: J. Organometal. Chem. 25, C27 (1970)

    Article  CAS  Google Scholar 

  6. Pijselman, J., Pereyre, M.: J. Organometal. Chem. 63, 139 (1973)

    Article  CAS  Google Scholar 

  7. Lewis, E.S., Grinstein, R.H.: J. Am. Chem. Soc. 84, 1158 (1962)

    Article  CAS  Google Scholar 

  8. O’Ferrall, R.A.M.: J. Chem. Soc. B, 785 (1970)

    Google Scholar 

  9. Grady, F.L., Kuivila, H.G.: J. Org. Chem. 34, 2014 (1969)

    Article  CAS  Google Scholar 

  10. Barnes, M.W., Patterson, J.M.: J. Org. Chem. 41, 733 (1976)

    Article  CAS  Google Scholar 

  11. Lipowitz, J., Bowman, S.A.: J. Org. Chem. 38, 162 (1973)

    Article  CAS  Google Scholar 

  12. Ueno, Y., Okawara, M.: J. Am. Chem. Soc. 101, 1893 (1979)

    Article  CAS  Google Scholar 

  13. For a Review of Silyl Radicals see Davidson, I.M.T., J. Chem. Soc. Quarterly Review, 25, 111 (1971)

    Google Scholar 

  14. Nagai, Y., Yamazaki, K., Shiojima, I., Kobori, N., Hayashi, N.: J. Organometal. Chem. 9, P21 (1967)

    Article  CAS  Google Scholar 

  15. Curtice, J., Gilman, H., Hammond, G.S.: J. Am. Chem. Soc. 79, 4754 (1957)

    Article  CAS  Google Scholar 

  16. Kerr, J.A., Smith, B.J.A., Trotman-Dickenson, A.F., Young, J.C.: J. Chem. Soc. Chem. Commun. 157 (1966)

    Google Scholar 

  17. Kerr, J.A., Smith, B.J.A., Trotman-Dickenson, A.F., Young, J.C.: J. Chem. Soc. A, 510 (1968)

    Google Scholar 

  18. Nagai, Y., Yamazaki, K., Shiojima, I.: J. Organometal. Chem. 9, P25 (1967)

    Article  Google Scholar 

  19. Ando, T., Hosaka, H., Funasaka, W., Yamanaka, H.: Bull. Soc. Chem. Japan, 46, 3513 (1973)

    Article  CAS  Google Scholar 

  20. Billingham, N.C., Jackson, R.A., Malek, F.: J. Chem. Soc. Chem. Commun. 344 (1977)

    Google Scholar 

  21. Citron, J.D.: J. Org. Chem. 36, 2547 (1971)

    Article  CAS  Google Scholar 

  22. Nakao, R., Fukumoto, T., Tsurugi, J.: J. Org. Chem. 37, 76 (1972)

    Article  Google Scholar 

  23. Nagata, Y., Dohmaru, T., Tsurugi, J.: J. Org. Chem. 38, 795 (1973)

    Article  CAS  Google Scholar 

  24. Nakao, R., Fukumoto, T., Tsurugi, J.: J. Org. Chem. 37, 4349 (1972)

    Article  CAS  Google Scholar 

  25. Benkeser, R.A.: Accts. Chem. Res. 4, 94 (1971)

    Article  CAS  Google Scholar 

  26. Benkeser, R.A., Smith, W.E.: J. Am. Chem. Soc. 90, 5307 (1968)

    Article  CAS  Google Scholar 

  27. Matsumoto, H., Ohkawa, K., Nakano, T., Nagai, Y.: Chem. Lett. 721 (1980)

    Google Scholar 

  28. Benkeser, R.A., Gaul, J.M., Smith,W.E.: J. Am. Chem. Soc. 91, 3666 (1969)

    Article  CAS  Google Scholar 

  29. Burg, A.B.: J. Am. Chem. Soc. 76, 2674 (1954)

    Article  CAS  Google Scholar 

  30. Benkeser, R.A., Foley, K.M., Grutzner, J.B., Smith, W.E.: J. Am. Chem. Soc. 92, 697 (1970)

    Article  CAS  Google Scholar 

  31. Bernstein, S.C.: J. Am. Chem. Soc. 92, 699 (1970)

    Article  CAS  Google Scholar 

  32. Nametkin, N.S., Kuz’min, O.V., Korolev, V.K., Kobrakov, K.I., Patriekeev, A.V.: Izv. Akad. Nauk SSSR, 676 (1978)

    Google Scholar 

  33. Nametkin, N.S., Kuz’min, O.V., Korolev, V.K., Kobrakov, K.I.: Dokl. Akad. Nauk. SSSR, 234, 340 (1977)

    CAS  Google Scholar 

  34. Benkeser, R.A., Smith, W.E.: J. Am. Chem. Soc. 91, 1556 (1969)

    Article  CAS  Google Scholar 

  35. Benkeser, R.A., Li, G.S., Mozdzen, E.C.: J. Organometal. Chem. 178, 21 (1979)

    Article  CAS  Google Scholar 

  36. Eaborn, C., “Organosilicon Compounds”, pp. 143–146, London: Buttersworth, 1960

    Google Scholar 

  37. Benkeser, R.A., Gaul, J.M.: J. Am. Chem. Soc. 92, 720 (1970)

    Article  CAS  Google Scholar 

  38. Benkeser, R.A., Foley, K.M., Gaul, J.M., Li, G.S.: J. Am. Chem. Soc. 92, 3232 (1970)

    Article  CAS  Google Scholar 

  39. Benkeser, R.A., Mozdzen, E.C., Muth, C.L.: J. Org. Chem. 44, 2185 (1979)

    Article  CAS  Google Scholar 

  40. Buckle, D.R., Morgan, N.J., Alexander, R.G.: J. Chem. Soc. Perkin I, 3004 (1979)

    Article  Google Scholar 

  41. Adcock, W., Dewar, M.J.S., Golden, R., Zeb, M.A.: J. Am. Chem. Soc. 97, 2198 (1975)

    Article  CAS  Google Scholar 

  42. Adcock, W., Alste, J., Rizui, S.Q.A., Aurangzeb, M.: J. Am. Chem. Soc. 98, 1701 (1976)

    Article  CAS  Google Scholar 

  43. Clarke, K., Gregory, D.N., Scrowston, R.M.: J. Chem. Soc. Perkin I, 63 (1977)

    Article  Google Scholar 

  44. Korpiun, O., Lewis, R.A., Chickos, J., Mislow, K.: J. Am. Chem. Soc. 90, 4842 (1968)

    Article  CAS  Google Scholar 

  45. Fritzsche, H., Hasserodt, U., Korte, F.: Chem. Ber. 97, 1988 (1964)

    Article  CAS  Google Scholar 

  46. Homer, L., Balzer, W.D.: Tetrahedron Lett. 1157 (1965)

    Google Scholar 

  47. Naumann, K., Zon, G., Mislow, K.: J. Am. Chem. Soc. 91, 7012 (1969)

    Article  CAS  Google Scholar 

  48. Naumann, K., Zon, G., Mislow, K.: J. Am. Chem. Soc. 91, 2788 (1969)

    Article  CAS  Google Scholar 

  49. Knowles, W.S., Sabacky, M.J., Vineyard, B.D., Weinkauff, D.J.: J. Am. Chem. Soc. 97, 2567 (1975)

    Article  CAS  Google Scholar 

  50. Tanao, K., Yamamoto, H., Matsumoto, H., Miyake, N., Hayashi, T., Kumada, M.: Tetrahedron Lett. 1389 (1977)

    Google Scholar 

  51. Cremer, S.E., Chorvat, R.J.: J. Org. Chem. 32, 4066 (1967)

    Article  CAS  Google Scholar 

  52. DeBruin, K.E., Zon, G., Naumann, K., Mislow, K.: J. Am. Chem. Soc. 91, 7027 (1969)

    Article  CAS  Google Scholar 

  53. Katz, T.J., Carnahan, Jr., J.C., Clarke, G.M., Acton, N.: J. Am. Chem. Soc. 92, 734 (1970)

    Article  CAS  Google Scholar 

  54. Turnblom, E.W., Katz, T.J.: J. Am. Chem. Soc. 93, 4065 (1971)

    Article  Google Scholar 

  55. Turnblom, E.W., Katz, T.J.: J. Am. Chem. Soc. 95, 4292 (1973)

    Article  CAS  Google Scholar 

  56. Baccolini, G., Todesco, P.E.: J. Org. Chem. 40, 2318 (1975)

    Article  CAS  Google Scholar 

  57. Chan, T.H., Ong, B.S.: J. Org. Chem. 39, 1748 (1974)

    Article  CAS  Google Scholar 

  58. Myers, D.K., Quin, L.D.: J. Org. Chem. 36, 1285 (1971)

    Article  CAS  Google Scholar 

  59. Marsi, K.L.: J. Am. Chem. Soc. 91, 4724 (1969)

    Article  CAS  Google Scholar 

  60. Egan, W., Chauviere, G., Mislow, K., Clark, R.T., Marsi, K.L.: J. Chem. Soc. Chem. Commun. 733 (1970)

    Google Scholar 

  61. Marsi, K.L.: J. Org. Chem. 39, 265 (1974)

    Article  Google Scholar 

  62. Marsi, K.L., Tuinstra, H.: J. Org. Chem. 40, 1843 (1975)

    Article  CAS  Google Scholar 

  63. Fisher, C., Mosher, H.S.: Tetrahedron Lett. 2487 (1977)

    Google Scholar 

  64. Symmes, Jr., C., Quin, L.D.: Tetrahedron Lett. 1853 (1976)

    Google Scholar 

  65. Quin, L.D., Symmes, Jr., C., Middlemas, E.D., Lawson, H.F.: J. Org. Chem. 45, 4688 (1980)

    Article  CAS  Google Scholar 

  66. Benkeser, R.A., Landesman, H., Foster, D.J.: J. Am. Chem. Soc. 74, 648 (1952)

    Article  CAS  Google Scholar 

  67. Zon, G., DeBruin, K.E., Naumann, K., Mislow, K.: J. Am. Chem. Soc. 91, 7023 (1969)

    Article  CAS  Google Scholar 

  68. Fritzsche, H., Hasserodt, U., Korte, F.: Chem. Ber. 98, 1681 (1965)

    Article  Google Scholar 

  69. Chan, T.H., Melnyk, A., Harpp, D.N.: Tetrahedron Lett. 201 (1969)

    Google Scholar 

  70. Chan, T.H., Melnyk, A.: J. Am. Chem. Soc. 92, 3718 (1970)

    Article  CAS  Google Scholar 

  71. Olah, G.A., Narang, S.C., Gupta, B.G.B., Malhotra, R.: Synthesis, 61 (1979)

    Google Scholar 

  72. Olah, G.A., Gupta, B.G.B., Narang, S.C.: Synthesis, 583 (1977)

    Google Scholar 

  73. Olah, G.A., Narang, S.C., Gupta, B.G.B., Malhotra, R.: Angew. Chem. Int. Ed. 18, 612 (1979)

    Article  Google Scholar 

  74. Nicolaou, K.C., Barnette, W.E., Magolda, R.L.: J. Am. Chem. Soc. 100, 2567 (1978)

    Article  CAS  Google Scholar 

  75. Schmidt, A.H., Russ, M.: Chem. Ber. 114, 1099 (1981)

    Article  CAS  Google Scholar 

  76. Goossens, J.C., Fr. Pat. 1, 456, 981 (1966)

    Google Scholar 

  77. Goossens, J.C., CA. 67, 54239 (1967)

    Google Scholar 

  78. Schmidt, A.H., Russ, M.: Chem. Ber. 114, 822 (1981)

    Article  CAS  Google Scholar 

  79. Soysa, H.S.D., Weber, W.P.: Tetrahedron Lett. 235 (1978)

    Google Scholar 

  80. Numata, T., Togo, H., Oae, S.: Chem. Lett. 329 (1979)

    Google Scholar 

  81. Detty, M.R.: J. Org. Chem. 44, 4528 (1979)

    Article  CAS  Google Scholar 

  82. Chan, T.H., Montillier, J.P., Van Horn, W.F., Harpp, D.N.: J. Am. Chem. Soc. 92, 7224 (1970)

    Article  CAS  Google Scholar 

  83. Olah, G.A., Narang, S.C., Fields, L.D., Salem, G.F.: J. Org. Chem. 44, 4792 (1980)

    Article  Google Scholar 

  84. Oae, S., Togo, H., Numata, T., Fujimori, K.: Chem. Lett. 1193 (1980)

    Google Scholar 

  85. Hortmann, A.G., Harris, R.L.: J. Am. Chem. Soc. 92, 1803 (1970)

    Article  CAS  Google Scholar 

  86. Tsui, F.P., Vogel, T.M., Zon, G.: J. Org. Chem. 40, 761 (1975)

    Article  CAS  Google Scholar 

  87. Cadogan, J.I.G.: J. Chem. Soc. Quarterly, Review, 22, 222 (1968)

    Article  CAS  Google Scholar 

  88. Hortmann, A.G., Koo, J.Y., Yu, C.C.: J. Org. Chem. 43, 2289 (1978)

    Article  CAS  Google Scholar 

  89. Sakurai, H., Kira, M., Kumada, M.: Bull. Chem. Soc. Japan, 44, 1167 (1971)

    Article  CAS  Google Scholar 

  90. Snyder, J.P., Lee, L., Bandurco, V.T., Yu, C.Y., Boyd, R.J.: J. Am. Chem. Soc. 94, 3260 (1972)

    Article  CAS  Google Scholar 

  91. Snyder, J.P., Heyman, M.L., Suciu, E.N.: J. Org. Chem. 40, 1395 (1975)

    Article  CAS  Google Scholar 

  92. Olsen, H., Snyder, J.P.: J. Am. Chem. Soc. 99, 1524 (1977)

    Article  CAS  Google Scholar 

  93. Greene, F.D., Gilbert, K.E.: J. Org. Chem. 40, 1409 (1975)

    Article  CAS  Google Scholar 

  94. Olah, G.A., Arvanaghi, M., Vankar, Y.D.: J. Org. Chem. 45, 3531 (1980)

    Article  CAS  Google Scholar 

  95. Ho, T.L.: Syn. Commun. 11, 101 (1981)

    Article  CAS  Google Scholar 

  96. Croft, T.S., McBrady, J.J.: J. Org. Chem. 41, 2256 (1976)

    Article  CAS  Google Scholar 

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© 1983 Springer-Verlag Berlin Heidelberg

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Weber, W.P. (1983). Miscellaneous Reductions. In: Silicon Reagents for Organic Synthesis. Reactivity and Structure Concepts in Organic Chemistry, vol 14. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68661-0_20

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  • DOI: https://doi.org/10.1007/978-3-642-68661-0_20

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