Abstract
Some of the fundamentals of silicon chemistry have been presented in Chapter One. We now consider one of the most versatile of the silicon reagents: trimethylsilyl cyanide (TMS-CN). Its reactivity effectively illustrates one of the fundamentals of silicon chemistry. Specifically, the trimethylsilyl group often reacts as if it were a proton. One might therefore expect TMS-CN to approximate the reactions and toxicity of hydrogen cyanide.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Evans, D.A., Truesdale, L.K.: Tetrahedron Lett. 4929 (1973)
Lidy, W., Sundermeyer, W.: Chem. Ber. 106, 587 (1973)
Evans, D.A., Truesdale, L.K., Carroll, G.L.: J. C. S. Chem. Commun. 55 (1973)
Evans, D.A., Carroll, G.L., Truesdale, L.K.: J. Org. Chem. 39, 914 (1974)
Fleming, I., Woolias, M.: J. Chem. Soc. Perkin I, 829 (1979)
Grunewald, G.L., Brouillette, W.J., Finney, J.A.: Tetrahedron Lett. 1219 (1980)
Corey, E.J., Tius, M.A., Das, J.: J. Am. Chem. Soc. 102, 1742 (1980)
Demina, M.M., Medvedeva, A.S., Protsuk, N.I., Vyazankin, N.S.: Zhur. Obsh. Khim. 48, 1563 (1978)
Stork, G., Kraus, G.: J. Am. Chem. Soc. 98, 6747 (1976)
Voronkov, M.G., Keiko, N.A., Kuznetsova, T.A., Tsetlina, E.O.: Zhur. Obsh. Khim. 48, 2138 (1978)
Ryu, I., Murai, S., Shinonaga, A., Horiike, T., Sonoda, N.: J. Org. Chem., 43, 780 (1978)
Parham, W.E., Roosevelt, C.S.: Tetrahedron Lett. 923 (1971)
Parham, W.E., Roosevelt, C.S.: J. Org. Chem. 37, 1975 (1972)
Frisch, K.C., Wolf, M.: J. Org. Chem. I8, 657 (1953)
Ebsworth, E.A.V., in “Organometallic Chemistry of the Group IV Elements” Vol. I, part I, (MacDiarmid, A.G., Ed.) p. 46. New York: Marcel Dekker, 1968
Cottrell, T.L., “The Strength of Chemical Bonds”, London: Butterworths 1958
Booth, M.R., Frankiss, S.G.: Spectrochim. Acta. Part A 26, 859 (1970)
Seckar, J.A., Thayer, J.S.: Inorganic Chem. 15, 501 (1976)
Seyferth, D., Kahlen, N.: J. Am. Chem. Soc. 82, 1080 (1960)
Ojima, I., Inaba, S.I., Nagai, Y.: Chem. Lett 737 (1975)
Ojima, I., Inaba, S.I., Nakatsugawa, K., Nagai, Y.: Chem. Lett. 331 (1975)
Lazukina, L.A., Kukhar, V.P.: Synthesis, 747 (1979)
Gassman, P.G., Talley, J.J.: Tetrahedron Lett., 3773 (1978)
Boutte, D., Auronx, A., Demande, Fr.: 2, 321, 484 Chem. Abst. 88, P37454i
Gassman, P.G., Talley, J.J.: J. Am. Chem. Soc. 102, 4138 (1980)
Oda, M., Yamamuro, A., Watabe, T.: Chem. Lett. 1427 (1979)
Takadate, A., Fishman, J.: J. Org. Chem. 44, 67 (1979)
Bartholow, R.M., Walaszek, E.J.: J. Med. Chem. 19, 189 (1976)
Smith, P.A.S., Baer, D.R.: Org. React. 11, 157 (1960)
Takaishi, N., Fujikura, Y., Inamoto, Y., Aigami, K.: J. Org. Chem. 42, 1737 (1977)
Thies, R.W., Seitz, E.P.: J. Org. Chem. 43, 1050 (1978)
Thies, R.W., Yue, S.: J.C. S. Chem. Commun. 950 (1980)
Dauben, Jr., H.J., Ringold, H.J., Wade, R.H., Anderson, A.G. Jr.: J. Am. Chem. Soc. 73, 2359 (1951)
Deuchert, K., Hertenstein, U., Hünig, S.: Synthesis, 777 (1973)
Hertenstein, U., Hünig, S., Oiler, M.: Synthesis, 416 (1976)
Utimoto, K., Obayashi, N., Shishiyama, Y., Inoue, M., Nozaki, H.: Tetrahedron Lett. 3389 (1980)
Amouroux, R., Axiotis, G.P.: Synthesis, 270 (1981)
Evans, D.A., Hoffman, J.M., Truesdale, L.K.: J. Am. Chem. Soc. 95, 5822 (1973)
Evans, D.A., Wong, R.Y.: J. Org. Chem. 42, 350 (1977)
Evans, D.A., Cain, P.A., Wong, R.Y.: J. Am. Chem. Soc. 99, 7083 (1977)
Evans, D.A., Hoffman, J.M.: J. Am. Chem. Soc. 98, 1983 (1976)
Hegedus, L.S., Evans, B.R.: J. Am. Chem. Soc. 100, 3461 (1978)
Hünig, S., Wehner, G.: Synthesis, 180 (1975)
Deuchert, K., Hertenstein, U., Hünig, S., Wehner, G.: Chem. Ber. 112, 2045 (1979)
Hünig, S., Wehner, G.: Synthesis, 391 (1975)
Hünig, S., Oiler, M.: Chem. Ber. 114, 959 (1981)
Hertenstein, U., Hünig, S., Oiler, M.: Chem. Ber. 113, 3783 (1980)
Ziegler, F.E., Nelson, R.V., Wong, T.F.: Tetrahedron Lett. 2125 (1980)
Heermann, K., Simchen, G.: Synthesis, 204 (1979)
Lidy, W., Sundermeyer, W.: Tetrahedron Lett. 1449 (1973)
Childs, M.E., Weber, W.P.: J. Org. Chem. 41, 3486 (1970)
Hertenstein, U., Hünig, S.: Angew. Chem. Int. Ed. 14, 179 (1975)
Voronkov, M.G., Keiko, N.A., Kuznetsova, T.A., Keiko, V.V., Tsetlina, E.O., Pestunovich, V.A.: Izv. Akad. Nauk. SSSR Ser. Khim. 906 (1978)
Ojima, I., Inaba, S.T., Nagai, Y.: J.C.S. Chem. Commun. 826 (1974)
Lutz, W., Sundermeyer, W.: Chem. Ber. 112, 2158 (1979)
Ojima, I., Inaba, S.I.: Tetrahedron Lett. 817 (1979)
Ojima, I., Inaba, S.I., Nagai, Y.: J. Organometallic Chem. 99, C5 (1975)
Asher, V., Becu, C., Anteunis, M.J.O., Callens, R.: Tetrahedron Lett. 141 (1981)
I opusinski, A., Michalski, J., Stec, W.J.: Angew. Chem. Int. 14, 108 (1975)
Lopusinski, A., Michalski, J., Stec, W.J.: Liebigs Ann. Chem. 924 (1977)
Harpp, D.N., Friedlander, B.T., Smith, R.A.: Synthesis, 181 (1979)
Harpp, D.N., Friedlander, B.T., Larsen, C., Steliou, K., Stockton, A.: J. Org. Chem. 43, 3481 (1978)
Nachbaur, E., Kosmus, W, Krannich, H.J., Sundermeyer, W.: Monat. für Chem. 109, 1211 (1978)
Evers, K.C., Freitag, W.O., Keith, J.N., Kriner, W.A., MacDiarmid, A.G., Sujishi, S.: J. Am. Chem. Soc. 81, 4493 (1959)
Ryu, I., Murai, S., Horiike, T., Shinonaga, A., Sonoda, N.: Synthesis, 154 (1978)
Taylor, E.C., Andrade, J.G., John, K.C., McKillop, A.: J. Org. Chem. 43, 2280 (1978)
Zubrick, J.W., Dunbar, B.I., Durst, H.D.: Tetrahedron Lett., 71 (1975)
Uznanski, B., Stec, W.J.: Synthesis, 154 (1978)
Häbich, D., Effenberger, F.: Synthesis, 755 (1978)
Lazukina, L.A., Kukhar, V.P., Pesotskaya, G.V.: Zhur. Obsh. Khim. 45, 2100 (1975)
Hünig, S., Wehner, G.: Synthesis, 522 (1979)
Rasmussen, J.K., Heilmann, S.M.: Synthesis, 523 (1979)
Kantehner, W., Haug, E., Mergen, W.W.: Synthesis, 460 (1980)
Rasmussen J.K., Heilmann, S.M.: Synthesis, 219 (1978)
Gassman, P.G., Saito, K., Talley, J.J.: J. Am. Chem. Soc. 102, 7613 (1980)
Gassman, P.G., Talley, J.J.: Org. Syn. 60, 14 (1981)
Livinghouse, T.: Org. Syn. 60, 126 (1981)
Mullis, J.C., Weber, W.P.: J. Org. Chem. 47, 2873 (1982).
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1983 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Weber, W.P. (1983). Chemistry of Trimethylsilyl Cyanide. 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_2
Download citation
DOI: https://doi.org/10.1007/978-3-642-68661-0_2
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-68663-4
Online ISBN: 978-3-642-68661-0
eBook Packages: Springer Book Archive