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Vinyl Silanes

  • Chapter
Silicon Reagents for Organic Synthesis

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

Abstract

The material of this chapter has been divided into seven parts. The first six are concerned with synthetically useful reactions of β-halosilanes, vinyl silanes, and α-silyl epoxides. The seventh deals with the preparation of vinyl silanes.

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References

  1. Sommer, L.H., Braughman, G.A.: J. Am. Chem. Soc. 83, 3346 (1961)

    Article  CAS  Google Scholar 

  2. Traylor, T.G., Hanstein, W., Berwin, H.J., Clinton, N.A., Brown, R.S.: J. Am. Chem. Soc. 93, 5715 (1971)

    Article  CAS  Google Scholar 

  3. Jarvie, A.W.P., Holt, A., Thompson, J.: J. Chem. Soc. B, 852 (1969)

    Google Scholar 

  4. Fleming, I., Goldhill, J.: J. Chem. Soc. Chem. Comm. 176 (1978)

    Google Scholar 

  5. Fleming, I., Goldhill, J.: J. Chem. Soc. Perkin I, 1493 (1980)

    Google Scholar 

  6. Eberson, L.: Acta Chem. Scand. 10, 633 (1956)

    Article  CAS  Google Scholar 

  7. Gilman, H., Lichtenwalter, G.D.: J. Am. Chem. Soc. 80, 608 (1958)

    Article  CAS  Google Scholar 

  8. Ager, D.J. Fleming, I.: J. Chem. Soc. Chem. Comm. 177 (1978)

    Google Scholar 

  9. Brownbridge, P., Fleming, I., Pearce, A., Warren, S.: J. Chem. Soc. Chem. Comm. 751 (1976)

    Google Scholar 

  10. Fleming, I., Paterson, I., Pearce, A.: J. Chem. Soc. Perkin I, 256 (1981)

    Google Scholar 

  11. Fleming, I., Patel, S.K.: Tetrahedron Lett. 2321 (1981)

    Google Scholar 

  12. Thomas, E.J., Whitman, G.H.: J. Chem. Soc. Chem. Comm. 212 (1979)

    Google Scholar 

  13. Miller, R.B., McGarvey, G.: Syn. Comm. 7, 475 (1977)

    Article  CAS  Google Scholar 

  14. Miller, R.B., Reichenbach, T.: Tetrahedron Lett. 543 (1974)

    Google Scholar 

  15. Miller, R.B., McGarvey, G.: J. Org. Chem. 43, 4424 (1978)

    Article  CAS  Google Scholar 

  16. Pillot, J.P., Dunoguès, J., Calas, R.: Syn. Comm. 9, 395 (1979)

    Article  CAS  Google Scholar 

  17. Chan, T.H., Lau, P.W.K., Mychajlowskij, W.: Tetrahedron Lett. 3317 (1977)

    Google Scholar 

  18. Miller, R.B., McGarvey, G.: J. Org. Chem. 44, 4623 (1979)

    Article  CAS  Google Scholar 

  19. Miller, R.B., McGarvey, G.: Syn. Comm. 8, 291 (1978)

    Article  CAS  Google Scholar 

  20. Huynh, C., Linstrumelle, G.: Tetrahedron Lett. 1073 (1979)

    Google Scholar 

  21. Robbins, C.M., Whitman, G.H.: J. Chem. Soc. Chem. Comm. 697 (1976)

    Google Scholar 

  22. Hudrilik, P.F., Arcoleo, J.P., Schwartz, R.H., Misra, R.N., Rona, R.J.: Tetrahedron Lett. 591 (1977)

    Google Scholar 

  23. Hudrilik, P.F., Hudrilik, A.M., Rona, R.J., Misra, R.N., Withers, G.P.: J. Am. Chem. Soc. 99, 1993 (1977)

    Article  Google Scholar 

  24. Koenig, K.E., Weber, W.P.: Tetrahedron Lett. 2533 (1973)

    Google Scholar 

  25. Brook, A.G., Duff, J.M., Reynolds, W.F.: J. Organometal. Chem. 121, 293 (1976)

    Article  CAS  Google Scholar 

  26. Koenig, K.E., Weber, W.P.: J. Am. Chem. Soc. 95, 3416 (1973)

    Article  CAS  Google Scholar 

  27. Cook, M.A., Eaborn, C., Walton, D.R.M.: J. Organometal. Chem. 24, 301 (1970)

    Article  CAS  Google Scholar 

  28. Bourne, A.J., Jarvie, A.W.P.: J. Organometal. Chem. 24, 335 (1970)

    Article  CAS  Google Scholar 

  29. Utimoto, K., Kitai, M., Nozaki, H.: Tetrahedron Lett. 2825 (1975)

    Google Scholar 

  30. Hudrilik, P.F., Schwartz, R.H., Hogan, J.C.: J. Org. Chem. 44, 155 (1979)

    Article  Google Scholar 

  31. Büchi, G., Wüest, H.: Tetrahedron Lett. 4305 (1977)

    Google Scholar 

  32. Pillot, J.P., Dunoguès, J., Calas, R.: C.R. Acad. Sci, Paris, Ser. C, 789 (1974)

    Google Scholar 

  33. Fleming, I., Pearce, A.: J. Chem. Soc. Perkin I, 2485 (1980)

    Google Scholar 

  34. Fleming, I., Pearce, A.: J. Chem. Soc. Chem. Comm. 633 (1975)

    Google Scholar 

  35. Pillot, J.P., Dunoguès, J., Calas, R.: Bull. Soc. Chim Fr. 2143 (1975)

    Google Scholar 

  36. Woodward, R.B., Hoffman, R., “The Conservation of Orbital Symmetry”: Verlag. Chem. 58 (1971)

    Google Scholar 

  37. Fristad, W.E., Dime, D.S., Bailey, T.R., Paquette, L.A.: Tetrahedron Lett. 1999 (1979)

    Google Scholar 

  38. Paquette, L.A., Fristad, W.E., Dime, D.S., Bailey, T.R.: J. Org. Chem. 45, 3017 (1980)

    Article  CAS  Google Scholar 

  39. Nazarov, I.N., Zaretskaya, L.L.: Zh. Obsh. Khim. 27, 693 (1957)

    CAS  Google Scholar 

  40. Cooke, F., Schwindeman, J., Magnus, P.: Tetrahedron Lett. 1995 (1979)

    Google Scholar 

  41. Cooke, F., Moerck, R., Schwindeman, J., Magnus, P.: J. Org. Chem. 45, 1046 (1980)

    Article  CAS  Google Scholar 

  42. Yamamoto, K., Nunokawa, O., Tsuji, J.: Synthesis, 721 (1977)

    Google Scholar 

  43. Yamamoto, K., Yoshitake, J., Qui, N.T., Tsuji, J.: Chem. Lett., 859 (1978)

    Google Scholar 

  44. Weber, W.P., Felix, R.A., Willard, A.K., Koenig, K.E.: Tetrahedron Lett. 4701 (1971)

    Google Scholar 

  45. Isobe, M., Kitamura, M., Goto, T.: Chem. Lett. 331 (1980)

    Google Scholar 

  46. Isobe, M., Kitamura, M., Goto, T.: Tetrahedron Lett. 239 (1981)

    Google Scholar 

  47. Grobel, B.T., Seebach, D.: Chem. Ber. 110, 852 (1977)

    Article  Google Scholar 

  48. Stork, G., Ganem, B.: J. Am. Chem. Soc. 95, 6152 (1973)

    Article  CAS  Google Scholar 

  49. Boeckman, Jr., R.K.: J. Am. Chem. Soc. 95, 6867 (1973)

    Article  CAS  Google Scholar 

  50. Boeckman, Jr., R.K., Blum, D.M., Ganem, B.: Org. Syn. 58, 158 (1978)

    CAS  Google Scholar 

  51. Boeckman, Jr., R.K.: J. Am. Chem. Soc. 96, 6179 (1974)

    Article  CAS  Google Scholar 

  52. Ottolenghi, A., Fridkin, M., Zilkha, A.: Can. J. Chem. 41, 2977 (1963)

    Article  CAS  Google Scholar 

  53. Brook, A.G., Duff, J.M., Legrow, G.E.: J. Organometal. Chem. 122, 31 (1976)

    Article  CAS  Google Scholar 

  54. Boeckman, Jr., R.K., Blum, D.M., Ganem, B., Halvey, N.: Org. Syn. 58, 152 (1978)

    CAS  Google Scholar 

  55. Stork, G., Singh, J.: J. Am. Chem. Soc. 96, 6181 (1974)

    Article  CAS  Google Scholar 

  56. Eisch, J.J., Trainor, J.T.: J. Org. Chem. 28, 487 (1963)

    Article  CAS  Google Scholar 

  57. Sakurai, H., Hayashi, N., Kumada, M.: J. Organometal. Chem. 18, 351 (1969)

    Article  CAS  Google Scholar 

  58. Stork, G., Colvin, E.: J. Am. Chem. Soc. 93, 2080 (1971)

    Article  CAS  Google Scholar 

  59. Stork, G., Jung, M.E.: J. Am. Chem. Soc. 96, 3682 (1974)

    Article  CAS  Google Scholar 

  60. Stork, G., Jung, M.E., Colvin, E., Noei, Y.: J. Am. Chem. Soc. 96, 3684 (1974)

    Article  CAS  Google Scholar 

  61. Altnau, G., Rösch, L., Bohlmann, F., Lonitz, M.: Tetrahedron Lett. 4069 (1980)

    Google Scholar 

  62. Ehlinger, E., Magnus, P.: J. Am. Chem. Soc. 102, 5004 (1980)

    Article  CAS  Google Scholar 

  63. Boeckman, Jr., R.K., Bruza, K.J.: Tetrahedron Lett. 3365 (1974)

    Google Scholar 

  64. Boeckman, Jr., R.K., Bruza, K.J.: J. Org. Chem. 44, 4781 (1979)

    Article  CAS  Google Scholar 

  65. Han, Y.K., Paquette, L.A.: J. Org. Chem. 44, 3731 (1979)

    Article  CAS  Google Scholar 

  66. Cooke, F., Magnus, P.: J. Chem. Soc. Chem. Comm. 513 (1977)

    Google Scholar 

  67. Burford, C., Cooke, F., Ehlinger, E., Magnus, P.: J. Am. Chem. Soc. 99, 4536 (1977)

    Article  CAS  Google Scholar 

  68. Cook, M.A., Eaborn, C., Walton, D.R.M.: J. Organometal. Chem. 29, 389 (1971)

    Article  CAS  Google Scholar 

  69. Magnus, P., Roy, G.: J. Chem. Soc. Chem. Commun. 297 (1978)

    Google Scholar 

  70. Schollkopf, U., Scholz, H.U.: Synthesis, 271 (1976)

    Google Scholar 

  71. Seyferth, D., Dow, A.W., Menzel, H., Flood, T.C.: J. Am. Chem. Soc. 90, 1080 (1968)

    Article  CAS  Google Scholar 

  72. Fristad, W.E., Bailey, T.R., Paquette, L.A., Gleiter, R., Böhm, M.C.: J. Am. J. Am. Chem. Soc. 101, 4420 (1979)

    Article  CAS  Google Scholar 

  73. Chan, T.H., Mychajlowskij, W.: Tetrahedron Lett. 3479 (1974)

    Google Scholar 

  74. Chan, T.H., Lau, P.W.K., Li, M.P.: Tetrahedron Lett. 2667 (1976)

    Google Scholar 

  75. Hasan, I., Kishi, Y.: Tetrahedron Lett. 4229 (1980)

    Google Scholar 

  76. Fristad, W.E., Bailey, T.R., Paquette, L.A.: J. Org. Chem. 45, 3038 (1980)

    Article  Google Scholar 

  77. Eisch, J.J., Trainor, J.T.: J. Org. Chem. 28, 2870 (1963)

    Article  CAS  Google Scholar 

  78. Fristad, W.E., Bailey, T.R., Paquette, L.A.: J. Org. Chem. 43, 1620 (1978)

    Article  CAS  Google Scholar 

  79. Whitmore, F.C., Sommer, L.H., Gold, J., Van Strien, R.E.: J. Am. Chem. Soc. 69, 1551 (1947)

    Article  CAS  Google Scholar 

  80. Hauser, C.R., Hance, C.R.: J. Am. Chem. Soc. 74, 5091 (1952)

    Article  CAS  Google Scholar 

  81. Cunico, R.F.: J. Org. Chem. 36, 929 (1971)

    Article  CAS  Google Scholar 

  82. Laporterie, A., Dubac, J., Lesbre, M.: C. R. Acad. Sci. Paris, Ser. C, 278, 375 (1974)

    CAS  Google Scholar 

  83. Laporterie, A., Dubac, J., Lesbre, M.: J. Organometal. Chem. 101, 187 (1975)

    Article  CAS  Google Scholar 

  84. Lesbre, M., Laporterie, A., Dubac, J., Manuel, G.: C. R. Acad. Sci. Paris, Ser. C, 280, 787 (1975)

    CAS  Google Scholar 

  85. Laporterie, A., Dubac, J., Mazerolles, P.: J. Organometal. Chem. 202, C89 (1980)

    Article  CAS  Google Scholar 

  86. Laporterie, A., Dubac, J., Manuel, G., Déléris, G., Kowalski, J., Dunoguès, J., Calas, R.: Tetrahedron 34, 2669 (1978)

    Google Scholar 

  87. Ohashi, S., Ruch, W.E., Butler, G.B.: J. Org. Chem. 46, 614 (1981)

    Article  CAS  Google Scholar 

  88. Batt, D.G., Ganem, B.: Tetrahedron Lett. 3323 (1978)

    Google Scholar 

  89. Danheiser, R.L., Sand, H.: J. Org. Chem. 45, 4810 (1980)

    Article  CAS  Google Scholar 

  90. Mironov, V.F., Petrov, A.D., Pisarenko, V.V.: Dokl. Akad. Nauk. SSSR, 124, 102 (1959)

    CAS  Google Scholar 

  91. Weyenberg, D.R., German Federal Republic Patent 936, 445, December 15, 1955

    Google Scholar 

  92. Watanabe, H., Asami, M., Nagai, Y.: J. Organometal. Chem. 195, 363 (1980)

    Article  CAS  Google Scholar 

  93. Matsumoto, H., Nagashima, S., Kato, T., Nagai, Y.: Angew. Chem. Int. 17, 279 (1978)

    Article  Google Scholar 

  94. Nesmeyanov, A.N., Freidlina, R.K., Chukovskaya, E.C., Petrova, R.G., Belyaysky, A.B.: Tetrahedron, 17, 61 (1962)

    Google Scholar 

  95. Schroeder, M.A., Wrighton, M.S.: J. Organometal. Chem. 128, 345 (1977)

    Article  CAS  Google Scholar 

  96. Schepinov, S.A., Khidekef, M.L., Lagodzinskaya, G.V.: Izv. Akad. Nauk. SSSR, Ser. Khim. 2165 (1968)

    Google Scholar 

  97. Milian, A., Towns, E., Maitlis, P.M.: J. Chem. Soc. Chem. Comm. 673 (1981)

    Google Scholar 

  98. Seki, Y., Takeshita, K., Kawamoto, K., Murai, S., Sonoda, N.: Angew. Chem. Int. 19, 928 (1980)

    Article  Google Scholar 

  99. Benkeser, R.A., Burraus, M.L., Noise, L.E., Schisler, J.V.: J. Am. Chem. Soc. 83, 4385 (1961)

    Article  CAS  Google Scholar 

  100. Husk, G.R., Vilitchko, A.M.: J. Organometal. Chem. 49, 85 (1973)

    Article  CAS  Google Scholar 

  101. Cunico, R.F., Clayton, F.J.: J. Org. Chem. 41, 1480 (1976)

    Article  CAS  Google Scholar 

  102. Eisch, J.J., Foxton, M.W.: J. Org. Chem. 36, 3520 (1971)

    Article  CAS  Google Scholar 

  103. Ayalon-Chass, D., Ehlinger, E., Magnus, P.: J. Chem. Soc. Chem. Comm. 772 (1977)

    Google Scholar 

  104. Ehlinger, E., Magnus, P.: J. Chem. Soc. Chem. Comm. 421 (1979)

    Google Scholar 

  105. Dunoguès, J., Pillot, J.P., Duffaut, N., Calas, R.: C. R. Acad. Sci. Paris, Ser. C. 467 (1974)

    Google Scholar 

  106. Birkofer, L., Kühn, T.: Chem. Ber. 111, 3119 (1978)

    Article  CAS  Google Scholar 

  107. Yarosh, O.G., Voronkov, V.K., Komarov, N.V.: Izv. Akad. Nauk SSSR Ser. Khim. 875 (1971)

    Google Scholar 

  108. Komarov, N.V., Yarosh, O.G.: Izv. Akad. Nauk. SSSR Ser. Khim. 1573 (1971)

    Google Scholar 

  109. Weber, W.P., Willard, A.K., Boettger, H.G.: J. Org. Chem. 36, 1620 (1971)

    Article  CAS  Google Scholar 

  110. Zwiefel, G., On, H.P.: Synthesis, 803 (1980)

    Google Scholar 

  111. Bock, M., Seidel, H.: J. Organometal. Chem. 13, 87 (1968)

    Article  CAS  Google Scholar 

  112. Mironov, V.F., Petrov, A.D., Maksimova, N.G.: Izv. Akad. Nauk. SSSR, Otd. Khim. Nauk. 954 (1958)

    Google Scholar 

  113. Fritz, G., Grobe, J.: Z. Anorg. Allg. Chem. 309, 77 (1961)

    Article  CAS  Google Scholar 

  114. Dexheimer, E.M., Spialter, L.: J. Organometal. Chem. 107, 229 (1976)

    Article  CAS  Google Scholar 

  115. Soderquist, J.A., Hassner, A.: J. Am. Chem. Soc. 102, 1577 (1980)

    Article  CAS  Google Scholar 

  116. Soderquist, J.A., Hassner, A.: J. Org. Chem. 45, 541 (1980)

    Article  CAS  Google Scholar 

  117. Clinet, J.C., Linstrumelle, G.: Tetrahedron Lett. 3987 (1980)

    Google Scholar 

  118. Chan, T.H., Baldassarre, A., Massuda, D.: Synthesis, 801 (1976)

    Google Scholar 

  119. Nagendrappa, G.: Synthesis, 704 (1980)

    Google Scholar 

  120. Taylor, R.T., Degenhardt, C.R., Melega, W.P., Paquette, L.A.: Tetrahedron Lett. 159 (1977)

    Google Scholar 

  121. Chamberlin, A.R., Stemke, J.E., Bond, F.T.: J. Org. Chem. 43, 147 (1978)

    Article  CAS  Google Scholar 

  122. Eaborn, C., Jackson, R.A., Pearce, R.: J. Chem. Soc. Perkin. 1, 2055 (1974)

    Article  Google Scholar 

  123. Eaborn, C., Jackson, R.A., Peace, R.: J. Chem. Soc. Perkin I, 470 (1975)

    Google Scholar 

  124. Mychajlowskij, W., Chan, T.H.: Tetrahedron Lett. 4439 (1976)

    Google Scholar 

  125. Chan, T.H., Mychajlowskij, W., Ong, B.S., Harpp, D.N.: J. Organometal. Chem. 107, Cl (1976)

    Article  Google Scholar 

  126. Uchida, K., Utimoto, K., Nozaki, H.: J. Org. Chem. 41, 2941 (1976)

    Article  CAS  Google Scholar 

  127. Obayashi, M., Utimoto, K., Nozaki, H.: Tetrahedron Lett. 1807 (1977)

    Google Scholar 

  128. Westmijze, H., Meijer, J., Vermeer, P.: Tetrahedron Lett. 1823 (1977)

    Google Scholar 

  129. Eisch, J.J., Damasevitz, G.A.: J. Org. Chem. 41, 2214 (1976)

    Article  CAS  Google Scholar 

  130. Uchida, K., Utimoto, K., Nozaki, H.: J. Org. Chem. 41, 2215 (1976)

    Article  CAS  Google Scholar 

  131. Fleming, I., Roessler, F.: J. Chem. Soc. Chem. Comm. 276 (1980)

    Google Scholar 

  132. Sato, F., Ishikawa, H., Sato, M.: Tetrahedron Lett. 85(1981)

    Google Scholar 

  133. Calas, R., Dunoguès, J.: C.R. Acad. Sci. Paris, Ser. C, 554 (1971)

    Google Scholar 

  134. Dunoguès, J., Bourgeois, P., Pillot, J.P., Merault, G., Calas, R., Lapouyade, P.: J. Organometal. Chem. 87, 169 (1975)

    Article  Google Scholar 

  135. Frisch, K.C., Young, R.B.: J. Am. Chem. Soc. 74, 4853 (1952)

    Article  CAS  Google Scholar 

  136. Sakurai, H., Nishiwaki, K.I., Kira, M.: Tetrahedron Lett. 4193 (1973)

    Google Scholar 

  137. Utimoto, K., Kitai, M., Naruse, M., Nozaki, H.: Tetrahedron Lett. 4233 (1975)

    Google Scholar 

  138. Binger, P., Köster, R.: Synthesis, 309 (1973)

    Google Scholar 

  139. Köster, R., Hagelee, L.A.: Synthesis, 118 (1976)

    Google Scholar 

  140. Snider, B.B., Karras, M., Conn, R.S.E.: J. Am. Chem. Soc. 100, 4624 (1978)

    Article  CAS  Google Scholar 

  141. Snider, B.B., Conn, R.S.E., Karras, M.: Tetrahedron Lett. 1679 (1979)

    Google Scholar 

  142. Amouroux, R., Chan, T.H.: Tetrahedron Lett. 4453 (1978)

    Google Scholar 

  143. Overman, L.E., Bell, K.L.: J. Am. Chem. Soc. 103, 1851 (1981)

    Article  CAS  Google Scholar 

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  1. Department of Chemistry, University of Southern California, 90007, University Park, Los Angeles, CA, USA

    William P. Weber

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Weber, W.P. (1983). Vinyl Silanes. 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_7

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