Abstract
Allylic trimethylsilanes are highly versatile synthetic intermediates. We will consider five aspects of their chemistry in this chapter. First will be electrophilic substitution reactions; second, cycloaddition reactions; third, synthesis of allylic silanes; fourth, reactions of silyl substituted allylic anions, and fifth, the chemistry of boron substituted allylic silanes.
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Sommer, L.H., Tyler, L.J., Whitmore, F.C.: J. Am. Chem. Soc. 70, 2872 (1948)
Carter, M.J., Fleming, I.: J. Chem. Soc. Chem. Commun. 679 (1976)
Coughlin, D.J., Salomon, R.G.: J. Org. Chem. 44, 3784 (1979)
Dunoguès, J., Arréguy, B., Biran, C., Calas, R., Pisciotti, F.: J. Organometal. Chem. 63, 119 (1973)
Fleming, I., Paterson, I.: Synthesis, 446 (1979)
Pandy-Szekeres, D., Déléris, G., Picard, J.P., Pillot, J.P., Calas, R.: Tetrahedron Lett. 4267 (1980)
Moritz, T., Okamoto, Y., Sakurai, H.: Tetrahedron Lett. 835 (1980)
Hosomi, A., Sakurai, H.: Chem. Lett. 85 (1981)
Woell, J.B., Boudjouk, P.: J. Org. Chem. 45, 5213 (1980)
Fleming, I., Au-Yeung, B.W.: Tetrahedron, 37, 13 (1981)
Jung, M.E., Blumenkopf, T.A.: Tetrahedron Lett. 3657 (1978)
Calas, R., Dunoguès, J., Pillot, J.P., Biran, C., Pisciotti, F., Arréguy, R.: J. Organo-metal. Chem. 85, 149 (1975)
Pilot, J.P., Dunoguès, J., Calas, R.: Tetrahedron Lett. 1871 (1976)
Pillot, J.P., Déléris, G., Dunoguès, J., Calas, R.: J. Org. Chem. 44, 3397 (1979)
Ojima, I., Kumagai, M., Miyazawa, Y.: Tetrahedron Lett. 1385 (1980)
Laguerre, M., Dunoguès, J., Calas, R.: Tetrahedron Lett. 57 (1978)
Hosomi, A., Saito, M., Sakurai, H.: Tetrahedron Lett. 429 (1979)
Hosomi, A., Saito, M., Sakurai, H.: Tetrahedron Lett. 3783 (1980)
Ochiai, M., Fujita, E.: Tetrahedron Lett. 4369 (1980)
Hosomi, A., Hashimoto, H., Sakurai, H.: J. Org. Chem. 43, 2551 (1978)
Hiroi, K., Chen, L.M.: J. Chem. Soc. Chem. Commun. 377 (1981)
Still, W.C., MacDonald, T.L.: J. Org. Chem. 41, 3620 (1976)
Sakurai, H., Imai, T., Hosomi, A.: Tetrahedron Lett. 4045 (1977)
Pillot, J.P., Dunoguès, J., Calas, R.: Synthesis, 469 (1977)
Grignon-Dubois, M., Pilot, J.P., Dunoguès, J., Duffaut, N., Calas, R.: J. Organo-metal. Chem. 124, 135 (1977)
Itoh, K., Fukui, M., Kurachi, Y.: J. Chem. Soc. Chem. Commun. 500 (1977)
Kelly, L.F., Narula, A.S., Birch, A.J.: Tetrahedron Lett. 871 (1980)
O’Boyle, J.E., Nicholas, K.M.: Tetrahedron Lett. 1595 (1980)
Au-Yeung, B.W., Fleming, I.: J. Chem. Soc. Chem. Commun. 81 (1977)
Sasaki, T., Usuki, A., Ohno, M.: Tetrahedron Lett. 4925 (1978)
Sasaki, T., Usuki, A., Ohno, M.: J. Org. Chem. 45, 3559 (1980)
Hughes, L.R., Schmid, R., Johnson, W.S.: Bioorganic Chem. 8, 513 (1979)
Raganathan, S., Raganathan, D., Mehrotra, A.K.: J. Am. Chem. Soc. 96, 5261 (1974)
Abel, E.W., Rowley, R.J.: J. Organometal. Chem. 84, 199 (1975)
Déléris, G., Dunoguès, J., Calas, R.: J. Organometal. Chem. 93, 43 (1975)
Calas, R., Dunoguès, J., Déléris, G., Pisciotti, F.: J. Organometal. Chem. 69, C15 (1974)
Déléris, G., Dunoguès, J., Calas, R.: Tetrahedron Lett. 2449 (1976)
Hosomi, A., Sakurai, M.: Tetrahedron Lett. 1295 (1976)
Hosomi, A., Endo, M., Sakurai, H.: Chem. Lett. 941 (1976)
Hosomi, A., Sakurai, H.: Tetrahedron Lett. 2589 (1978)
Wilson, S.R., Phillips, L.R., Natalie, Jr., K.J.: J. Am. Chem. Soc. 101, 3340 (1979)
Kuwajima, I., Tanaka, T., Atsumi, K.: Chem. Lett. 779 (1979)
Itoh, A., Oshima, K., Nozaki, M.: Tetrahedron Lett. 1783 (1979)
Sarkar, T.K., Andersen, N.H.: Tetrahedron Lett. 3513 (1978)
Hosomi, A., Shirahata, A., Sakurai, H.: Tetrahedron Lett. 3043 (1978)
Fleming, I., Pearce, A., Snowden, R.L.: J. Chem. Soc. Chem. Commun. 182 (1976)
Itoh, K., Fukui, M., Kurachi, Y.: J. Chem. Soc. Chem. Commun. 500 (1977)
Itoh, K., Yogo, T., Ishii, Y.: Chem. Lett. 103 (1977)
Hosomi, A., Hashimoto, H., Sakurai, H.: Tetrahedron Lett. 951 (1980)
Hosomi, A., Saito, M., Sakurai, M.: Tetrahedron Lett. 3783 (1980)
Pornet, J.: Tetrahedron Lett. 2049 (1980)
Seyferth, D., Pornet, J.: J. Org. Chem. 45, 1721 (1980)
Sakurai, H., Sasaki, K., Hosomi, A.: Tetrahedron Lett. 745 (1981)
Hosomi, A., Sakurai, H.: Tetrahedron Lett. 4041 (1977)
Hosomi, A., Sakurai, H.: J. Am. Chem. Soc. 99, 1673 (1977)
Pardo, R., Zahra, J.P., Santelli, M.: Tetrahedron Lett. 4557 (1979)
Yanami, T., Miyashita, M., Yoshikoshi, A.: J. Chem. Soc. Chem. Commun. 525 (1979)
Yanami, T., Miyashita, M., Yoshikoshi, A.: J. Org. Chem. 45, 607 (1980)
Hosomi, A., Kobayashi, M., Sakurai, H.: Tetrahedron Lett. 955 (1980)
Knapp, S., O’Connor, U., Mobilio, D.: Tetrahedron Lett. 4557 (1980)
Hosomi, A., Hashimoto, H., Sakurai, H.: Chem. Lett. 245 (1979)
Jellal, A., Santelli, M.: Tetrahedron Lett. 4487 (1980)
Ochiai, M., Arimoto, M., Fujita, E.: Tetrahedron Lett. 1115 (1981)
Ojima, I., Kumagai, M.: Chem. Lett. 575 (1978)
Ojima, I., Miyazawa, Y., Kumagai, M.: J. Chem. Soc. Chem. Commun. 927 (1976)
Hartman, G.D., Traylor, T.G.: Tetrahedron Lett. 939 (1975)
Ochiai, M., Arimoto, M., Fujita, E.: J. Chem. Soc. Chem. Commun. 460 (1981)
Déléris, G., Dunoguès, J., Calas, R.: J. Organometal. Chem. 116, C45 (1976)
Au-Yeung, B.W., Fleming, I.: J. Chem. Soc. Chem. Commun. 81 (1977)
Trost, B.M., Chan, D.M.T.: J. Am. Chem. Soc. 101, 6429 (1979)
Trost, B.M., Chan, D.M.T.: J. Am. Chem. Soc. 101, 6432 (1979)
Hosomi, A., Saito, M., Sakurai, H.: Tetrahedron Lett. 355 (1980)
Slutsky, J., Kwart, H.: J. Am. Chem. Soc. 95, 8678 (1973)
Fleming, I., Percival, A.: J. Chem. Soc. Chem. Commun. 681 (1976)
Hurd, D.T.: J. Am. Chem. Soc. 67, 1813 (1945)
Rhone-Poulenc, French Patent 2, 051, 903 (1969)
Furuya, N., Sukawa, T.: J. Organometal. Chem. 96, C-1 (1975)
Lefort, M., Simmonet, C., Birot, M., Déléris, G., Dunoguès, J., Calas, R.: Tetrahedron Lett. 1857 (1980)
Matsumoto, H., Yako, T., Nagashima, S., Motegi, T., Nagai, Y.: J. Organometal. Chem. 148, 97 (1978)
Watanabe, H., Saito, M., Sutou, N., Nagai, Y.: J. Chem. Soc. Chem. Commun. 617 (1981)
Sakurai, H., Hosomi, A., Kumada, M.: Tetrahedron Lett. 2469 (1968)
Matsumoto, H., Shono, K., Wada, A., Matsubara, I., Watanabe, H., Nagai, Y.: J. Organometal. Chem. 199, 185 (1980)
Laguerre, M., Dunoguès, J., Calas, R., Duffaut, N.: J. Organometal. Chem. 112, 49 (1976)
Biran, C., Duffaut, N., Dunoguès, J., Calas, R.: J. Organometal. Chem. 91, 279 (1975)
Tzeng, D.J., Weber, W.P.: J. Org. Chem. 46, 281 (1981)
Déléris, G., Kowalski, J., Dunoguès, J., Calas, R.: Tetrahedron Lett. 4211 (1977)
Seyferth, D., Wursthorn, K.R., Lim, T.F.O., Sepelak, D.J.: J. Organometal. Chem. 181, 293 (1979)
Whitmore, F.C., Sommer, L.H.: J. Am. Chem. Soc. 68, 481 (1946)
Cooper, G.D., Prober, M.: J. Am. Chem. Soc. 76, 3943 (1954)
Eaborn, C., Jeffrey, J.C.: J. Chem. Soc. 4266 (1954)
Gopalan, A., Moerck, R., Magnus, P.: J. Chem. Soc. Chem. Commun. 548 (1979)
Hosomi, A., Shirahata, A., Sakurai, H.: Chem. Lett. 901 (1978)
Seyferth, D., Murphy, G.J., Woodruff, R.A.: J. Organometal. Chem. 141, 71 (1977)
Ahlbrecht, H., Eichler, J.: Synthesis, 672 (1974)
Cornu, R.J.P., Massé, J., Samate, D.: J. Organometal. Chem. 93, 71 (1975)
Cornu, R.J.P., Massé, J.: J. Organometal. Chem. 57, C5 (1973)
Corriu, R.J.P., Lanneau, G.F., Leclercq, D., Samate, D.: J. Organometal. Chem. 144, 155 (1978)
Ayalon-Chass, D., Ehlinger, E., Magnus, P.: J. Chem. Soc. Chem. Commun. 772 (1977)
Ehlinger, E., Magnus, P.: Tetrahedron Lett. 11 (1980)
Lau, P.W.K., Chan, T.H.: Tetrahedron Lett. 2383 (1978)
Seyferth, D., Mammarella, R.E.: J. Organometal. Chem. 156, 279 (1978)
Kow, R., Rathke, M.W.: J. Am. Chem. Soc. 95, 2715 (1973)
Yatagi, H., Yamamoto, Y., Maruyama, K.: J. Am. Chem. Soc. 102, 4548 (1980)
Yamamoto, Y., Yatagai, H., Maruyama, K.: J. Am. Chem. Soc. 103, 3229 (1981)
Tsai, D.J.S., Matteson, D.S.: Tetrahedron Lett. 2751 (1981)
Tsunoda, T., Suzuki, M., Noyori, R.: Tetrahedron Lett. 71 (1980)
Fleming, I., Pearce, A.: J. Chem. Soc. Perkin 1, 251 (1981)
Trost, B.M., Vincent, J.E.: J. Am. Chem. Soc. 102, 5680 (1980)
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© 1983 Springer-Verlag Berlin Heidelberg
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Weber, W.P. (1983). Allylic 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_11
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DOI: https://doi.org/10.1007/978-3-642-68661-0_11
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