Skip to main content
SpringerLink
Log in

Silyl Acetylenes

  • Chapter
Silicon Reagents for Organic Synthesis

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

Abstract

Silyl acetylenes have proved to be versatile reagents in a number of reactions. This chapter will be organized into five major sections: first, addition reactions to 1-silyl alkynes; second, electrophilic substitution reactions; third, the use of 1-silyl alkynes as protecting groups for terminal alkynes; fourth, cycloaddition reactions; and fifth, the preparation of these compounds.

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

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  3. Komarov, V.M., Yarosh, O.G.: Isv. Akad. Nauk. SSSR. Ser. Khim. 1573 (1971)

    Google Scholar 

  4. Yarosh, O.G., Vovenkov, V.K., Kamarov, N.V.: Izv. Akad. Nauk. SSSR Ser. Khim. 875 (1971)

    Google Scholar 

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

    Google Scholar 

  6. Zweifel, G., On, H.P.: Synthesis, 803 (1980)

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

  10. Miller, J.A., Zweifel, G.: Synthesis, 288 (1981)

    Google Scholar 

  11. Soto, F., Ishikawa, H., Soto, M.: Tetrahedron Lett. 85 (1981)

    Google Scholar 

  12. Obayashi, M., Utimoto, K., Nozaki, H.: Tetrahedron Lett. 1805 (1979)

    Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

  15. Flood, T., Peterson, P.E.: J. Org. Chem. 45, 5006 (1980)

    Article  Google Scholar 

  16. Bourgeois, P., Mérault, G.: J. Organometal. Chem. 39, C44 (1972)

    Article  CAS  Google Scholar 

  17. Schmid, R., Huesmann, P.L., Johnson, W.S.: J. Am. Chem. Soc. 102, 5122 (1980)

    Article  CAS  Google Scholar 

  18. Johnson, W.S., Yarnell, T.M., Myers, R.F., Morton, D.R.: Tetrahedron Lett. 2549 (1978)

    Google Scholar 

  19. Johnson, W.S., Frei, B., Gopalan, A.S.: J. Org. Chem. 46, 1512 (1981)

    Article  CAS  Google Scholar 

  20. Walton, D.R.M., Webb, M.J.: J. Organometal. Chem. 37, 41 (1972)

    Article  CAS  Google Scholar 

  21. Oliver, R., Walton, D.R.M.: Tetrahedron Lett. 5209 (1972)

    Google Scholar 

  22. Eiter, K., Lieb, F., Disselnkütter, H., Oediger, H.: Liebigs. Ann. Chem. 658, (1978)

    Google Scholar 

  23. Birkofer, L., Ritter, A., Uhlenbrauck, H.: Chem. Ber. 96, 3280 (1963)

    Article  CAS  Google Scholar 

  24. Utimoto, K., Tanaka, M., Kitai, M., Nozaki, H.: Tetrahedron Lett. 2301 (1978)

    Google Scholar 

  25. Ladika, M., Stang, P.J.: J.C.S. Chem. Commun. 459 (1981)

    Google Scholar 

  26. Walton, D.R.M., Waugh, F.: J. Organometal. Chem. 37, 45 (1972)

    Article  CAS  Google Scholar 

  27. Stang, P.J., Ladika, M.: Synthesis, 29 (1981)

    Google Scholar 

  28. Bourgeois, P., Merault, G., Calas, R.: J. Organometal. Chem. 59, C-4 (1973)

    Article  Google Scholar 

  29. Bhattacharya, S.N., Josiah, B.M., Walton, D.R.M.: Organometal. Chem. Synthesis, 1, 145 (1970/1971)

    Google Scholar 

  30. Bourgeois, P., Calas, R.: J. Organometal. Chem. 22, 89 (1970)

    Article  CAS  Google Scholar 

  31. Bourgeois, P., Mérault, G., Duffaut, N., Calas, R.: J. Organometal. Chem. 59, 145 (1973)

    Article  CAS  Google Scholar 

  32. Bourgeois, P., Mérault, G.: C.R. Acad. Sci. Paris Ser. C, 273, 714 (1971)

    CAS  Google Scholar 

  33. Bourgeois, P., Calas, R., Mérault, G.: J. Organometal. Chem. 141, 23 (1977)

    Article  CAS  Google Scholar 

  34. Calas, R., Dunoguès, J., Deleris, G., Pisciotti, F.: J. Organometal. Chem. 69, C15 (1974)

    Article  CAS  Google Scholar 

  35. Deleris, G., Dunoguès, J., Calas, R.: J. Organometal. Chem. 93, 43 (1975)

    Article  CAS  Google Scholar 

  36. Deleris, G., Dunoguès, J., Calas, R.: Tetrahedron Lett. 2449 (1976)

    Google Scholar 

  37. Nakamura, E., Kuwajima, I.: Angew. Chem. Int. Ed. 15, 498 (1976)

    Google Scholar 

  38. Holmes, A.B., Jennings-White, C.L.D., Schulthess, A.H., Akinde, B., Walton, D.R.M.: J. Chem. Soc. Chem. Commun. 840 (1979)

    Google Scholar 

  39. Pornet, J., Randrianoelina, B.: Tetrahedron Lett. 1327 (1981)

    Google Scholar 

  40. Pornet, J.: Tetrahedron Lett. 453 (1981)

    Google Scholar 

  41. Pornet, J.: Tetrahedron Lett. 2049 (1980)

    Google Scholar 

  42. Pornet, J.: Tetrahedron Lett. 455 (1981)

    Google Scholar 

  43. Sakurai, H., Sasaki, K., Hosomi, A.: Tetrahedron Lett. 745 (1981)

    Google Scholar 

  44. Danheiser, R.L., Carini, D.J.: J. Org. Chem. 45, 3925 (1980)

    Article  Google Scholar 

  45. Montury, M., Psaume, B., Gore, J.: Tetrahedron Lett. 163 (1980)

    Google Scholar 

  46. Danheiser, R.L., Carini, D.J., Basak, A.: J. Am. Chem. Soc. 103, 1604 (1981)

    Article  CAS  Google Scholar 

  47. Jellal, A., Santelli, M.: Tetrahedron Lett. 4487 (1980)

    Google Scholar 

  48. Kozar, L.G., Clark, R.D., Heathcock, C.H.: J. Org. Chem. 42, 1386 (1977)

    Article  CAS  Google Scholar 

  49. Casara, P., Metcalf, B.W.: Tetrahedron Lett. 1581 (1978)

    Google Scholar 

  50. Despo, A.D., Chiu, S.K., Flood, T., Peterson, P.E.: J. Am. Chem. Soc. 102, 5120 (1980)

    Article  CAS  Google Scholar 

  51. Shakhovskoi, B.G., Stadnichuk, M.D., Petrov, A.A.: J. Gen. Chem. USSR, 34, 2646 (1964)

    Google Scholar 

  52. Holmes, A.B. Raphel, R.A., Welland, N.K.: Tetrahedron Lett. 1539 (1976)

    Google Scholar 

  53. Schmidt, H.M., Arens, J.F.: Rec. Tray. Chim de bas Pays, 86, 1138 (1967)

    Article  CAS  Google Scholar 

  54. Corey, E.J., Kirst, H.A.: Tetrahedron Lett. 5041 (1968)

    Google Scholar 

  55. Corey, E.J., Katzenellenbogen, J.A., Gilman, N.W., Roman, S.A., Erickson, B.W.: J. Am. Chem. Soc. 90, 5618 (1968)

    Article  CAS  Google Scholar 

  56. Corey, E.J., Kirst, H.A., Katzenellenbogen, J.A.: J. Am. Chem. Soc. 92, 6314 (1970)

    Article  CAS  Google Scholar 

  57. Eaborn, C., Thompson, A.R., Walton, D.R.M.: J. Chem. Soc. C, 1364 (1967)

    Google Scholar 

  58. Metcalf, B.W., Jund, K.: Tetrahedron Lett. 3689 (1977)

    Google Scholar 

  59. Metcalf, B.W., Casara, P.: Tetrahedron Lett. 3337 (1975)

    Google Scholar 

  60. Gilman, H., Brook, A.G., Miller, L.S.: J. Am. Chem. Soc. 75, 4531 (1953)

    Article  CAS  Google Scholar 

  61. Eaborn, C., Walton, D.R.M.: J. Organometal. Chem. 4, 217 (1965)

    Article  CAS  Google Scholar 

  62. Eaborn, C., Thompson, A.R., Walton, D.R.M.: J. Organometal. Chem. 17, 149 (1969)

    Article  CAS  Google Scholar 

  63. Newman, H.: J. Org. Chem. 38, 2254 (1973)

    Article  CAS  Google Scholar 

  64. Hay, A.S.: J. Org. Chem. 27, 3320 (1962)

    Article  CAS  Google Scholar 

  65. Eastmond, R., Walton, D.R.M.: J. Chem. Soc., Chem. Commun. 204 (1968)

    Google Scholar 

  66. Eastmond, R., Johnson, T.R., Walton, D.R.M.: J. Organometal. Chem. 50, 87 (1973)

    Article  CAS  Google Scholar 

  67. McQuilkin, R.M., Garrett, P.J., Sondheimer, F.: J. Am. Chem. Soc. 92, 6682 (1970)

    Article  Google Scholar 

  68. Eglinton, G., McCrae, W.: Adv. Org. Chem. 4, 225 (1963)

    Google Scholar 

  69. Eaborn, C., Thompson, A.R., Walton, D.R.M.: J. Chem. Soc. B, 357 (1970)

    Google Scholar 

  70. Ghose, B.N., Walton, D.R.M.: Synthesis, 890 (1974)

    Google Scholar 

  71. Takahashi, S., Kuroyama, Y., Sonogashira, K., Hagihara, N.: Synthesis, 627 (1980)

    Google Scholar 

  72. Mitchell, R.H., Sondheimer, F.: Tetrahedron 26, 2141 (1970)

    Article  CAS  Google Scholar 

  73. Seyferth, D., Sarafidis, C., Evnin, A.B.: J. Organometal. Chem. 2, 417 (1964)

    Article  CAS  Google Scholar 

  74. Seyferth, D., White, D.L.: J. Organometal. Chem. 34, 119 (1972)

    Article  CAS  Google Scholar 

  75. Birkofer, L., Stilke, R.: J. Organometal. Chem. 74, C-1 (1974)

    Article  Google Scholar 

  76. Kloek, J.A.: J. Org. Chem. 46, 1951 (1981)

    Article  CAS  Google Scholar 

  77. Shchukovskaya, L.L., Budakova, L.D., Pal’chik, R.I.: Zhur. Obsh. Khim. 43, 1989 (1973)

    CAS  Google Scholar 

  78. Himbert, G.: Angew. Chem. 88, 59 (1976)

    Google Scholar 

  79. Henn, L., Himbert, G.: Chem. Ber. 114, 1015 (1981)

    Article  CAS  Google Scholar 

  80. Sato, Y., Kobayashi, Y., Sugiura, M., Shirai, H.: J. Org. Chem. 43, 199 (1978)

    Article  CAS  Google Scholar 

  81. Hübel, W., Hoogzand, C.: Chem. Ber. 93, 103 (1960)

    Article  Google Scholar 

  82. Greenfield, H., Sternberg, H.W., Friedel, R.A., Wotiz, J.H., Markby, R., Wender, I.: J. Am. Chem. Soc. 78, 120 (1965)

    Article  Google Scholar 

  83. Hillard, III, R.L., Vollhardt, K.P.C.: Angew. Chem. Int. Ed. 14, 712 (1975)

    Article  Google Scholar 

  84. Aalbersberg, W.G.L., Barkovich, A.J., Funk, R.L., Hillard, III, R.L., Vollhardt, K.P.C.: J. Am. Chem. Soc. 97, 5600 (1975)

    Article  CAS  Google Scholar 

  85. Hillard, III, R.L., Vollhardt, K.P.C.: Angew. Chem. Int. Ed. 16, 399 (1977)

    Google Scholar 

  86. Funk, R.L., Vollhardt, K.P.C.: J. Am. Chem. Soc. 99, 5483 (1977)

    Article  CAS  Google Scholar 

  87. Funk, R.L., Vollhardt, K.P.C.: J. Chem. Soc. Chem. Commun. 833 (1976)

    Google Scholar 

  88. Birkofer, L., Eichstüdt, D.: J. Organometal. Chem. 145, C29 (1978)

    Google Scholar 

  89. Birkofer, L., Stilke, R.: Chem. Ber. 107, 3717 (1974)

    Article  Google Scholar 

  90. Birkofer, L., Franz, M.: Chem. Ber. 100, 2681 (1967)

    Article  CAS  Google Scholar 

  91. Birkofer, L., Franz, M.: Chem. Ber. 105, 17 (1972)

    Google Scholar 

  92. Guillerm, G., Honoré, A.L., Veniard, L., Pourcelot, G., Benaim, J.: Bull. Soc. Chem. Fr. 2739 (1973)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  94. Seyferth, D., Flood, T.C.: J. Organometal. Chem. 29, C25 (1971)

    Article  CAS  Google Scholar 

  95. Birkofer, L., Wegner, P.: Chem. Ber. 99, 2512 (1966)

    Article  CAS  Google Scholar 

  96. Patrick, T.B., Haynie, E.C., Probst, W.J.: J. Org. Chem. 37, 1553 (1972)

    Article  CAS  Google Scholar 

  97. Slutsky, J., Kwart, H.: J. Am. Chem. Soc. 95, 8678 (1973)

    Article  CAS  Google Scholar 

  98. Eaborn, C., Walton, D.R.M.: J. Organometal. Chem. 4, 217 (1965)

    Article  CAS  Google Scholar 

  99. Holmes, A.B., Jones, G.E.: Tetrahedron Lett. 3111 (1980)

    Google Scholar 

  100. Mukaiyama, T., Soai, K., Sato, T., Shimizu, H., Suzuki, K.: J. Am. Chem. Soc. 101, 1455 (1979)

    Article  CAS  Google Scholar 

  101. Mukaiyama, T., Suzuki, K., Soai, K.., Sato, T.: Chem. Lett. 447 (1979)

    Google Scholar 

  102. Brinkmeyer, R.S., MacDonald, T.L.: J. Chem. Soc. Chem. Commun. 876 (1978)

    Google Scholar 

  103. MacDonald, T.L., Reagan, D.R., Brinkmeyer, R.S.: J. Org. Chem. 45, 4740 (1980)

    Article  CAS  Google Scholar 

  104. Ireland, R.E., Dawson, M.I., Lipinski, C.A.: Tetrahedron Lett. 2247 (1970)

    Google Scholar 

  105. Stork, G., Kowalski, C., Garcia, G.: J. Am. Chem. Soc. 97, 3258 (1975)

    Article  CAS  Google Scholar 

  106. Daniels, R.G., Paquette, L.A.: Tetrahedron Lett. 1579 (1981)

    Google Scholar 

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

    Article  CAS  Google Scholar 

  108. Yogo, T., Koshino, J., Suzuki, A.: Syn. Commun. 9, 809 (1979)

    Article  CAS  Google Scholar 

  109. Masson, J.C., Quan, M.L., Cadiot, P.: Bull. Soc. Chim. Fr. 777 (1967)

    Google Scholar 

  110. Chiu, S.K., Peterson, P.E.: Tetrahedron Lett. 4047 (1980)

    Google Scholar 

  111. Laguerre, M., Dunoguès, J., Calas, R.: J. Organometal. Chem. 145, C34 (1978)

    Article  CAS  Google Scholar 

  112. Beard, C.D., Craig, J.C.: J. Am. Chem. Soc. 96, 7950 (1974)

    Article  CAS  Google Scholar 

  113. Jaffe, F.: J. Organometal. Chem. 23, 53 (1970)

    Article  CAS  Google Scholar 

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

    Google Scholar 

  115. Yogo, T., Koshino, J., Suzuki, A.: Tetrahedron Lett. 1781 (1979)

    Google Scholar 

  116. Westmijze, H., Vermeer, P.: Synthesis, 390 (1979)

    Google Scholar 

  117. Ganem, B.: Tetrahedron Lett. 4467 (1974)

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    William P. Weber

Authors
  1. William P. Weber
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1983 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Weber, W.P. (1983). Silyl Acetylenes. 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_9

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-68661-0_9

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-68663-4

  • Online ISBN: 978-3-642-68661-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation