Abstract
Cyclomagnesation of terminal and cyclic olefins and 1,2-dienes with RMgHlg and R2Mg in the presence of dichloro(dicyclopentadienyl)titanium(IV) gives non-Grignard cyclic and acyclic organomagnesium compounds. The reaction direction depends on the structure of unsaturated initial compound. The most probable reaction mechanism is discussed.
Similar content being viewed by others
REFERENCES
Dzhemilev, U.M., Sultanov, R.M., Gaimaldinov, R.G., and Muslukhov, R.R., Primenenie metallokompleksnogo kataliza v organicheskom sinteze (Application of Metal-Complex Catalysis in Organic Synthesis), Ufa: Rossiya, 1989, p. 40.
Dzhemilev, U.M., Sultanov, R.M., Gaimaldinov, R.G., and Tolstikov, G.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1991, p. 1388.
Lewis, D.P., Muller, P.M., Whitby, R.J., and Jones, R.V.H., Tetrahedron Lett., 1991, vol. 32, p. 6797.
Dzhemilev, U.M., Sultanov, R.M., Gaimaldinov, R.G., Muslukhov, R.R., Lomakina, S.I., and Tolstikov, G.A., Izv. Ross. Akad. Nauk, Ser. Khim., 1992, p. 980.
Dzhemilev, U.M., Sultanov, R.M., and Gaimaldinov, R.G., Izv. Ross. Akad. Nauk, Ser. Khim., 1993, p. 165.
Knight, K.S., Wang, D., Waymouth, R.M., and Ziller, J., J. Am. Chem. Soc., 1994, vol. 116, p. 1845.
Dzhemilev, U.M., Sultanov, R.M., and Gaimaldinov, R.G., J. Organomet. Chem., 1995, vol. 491, p. 1.
Lewis, D.P., Whitby, R.J., and Jones, R.V.H., Tetrahedron, 1995, vol. 51, p. 4541.
Negishi, E., Rousset, C.J., Choueiry, D., Maye, J.P., Suzuki, N., and Takahashi, T., Inorg. Chim. Acta, 1998, vol. 280, p. 8.
Dzhemilev, U.M., Vostrikova, O.S., and Sultanov, R.M., Izv. Akad. Nauk SSSR, Ser. Khim., 1983, p. 218.
Dzhemilev, U.M., Vostrikova, O.S., and Sultanov, R.M., Izv. Akad. Nauk SSSR, Ser. Khim., 1984, p. 2053.
Dzhemilev, U.M., Vostrikova, O.S., and Sultanov, R.M., Izv. Akad. Nauk SSSR, Ser. Khim., 1985, p. 1430.
Dzhemilev, U.M. and Vostrikova, O.S., J. Organomet. Chem., 1985, vol. 285, p. 43.
Knight, K.S. and Waymouth, R.M., J. Am. Chem. Soc., 1991, vol. 113, p. 6268.
Lai, Y.-H., Synthesis, 1981, no. 8, p. 585.
Shur, V.B., Berkovich, E.G., and Vol’pin, M.E., J. Organomet. Chem., 1982, vol. 228, p. 36.
Grubbs, R.H. and Miyashita, A., Chem. Commun., 1977, vol. 23, p. 864.
Dzhemilev, U.M., Ibragimov, A.G., Khafizova, L.O., Gilyazev, R.R., and D’yakonov, V.A., Izv. Ross. Akad. Nauk, Ser. Khim., 2004, p. 130.
Ashby, E.C. and Ainslie, R.D., J. Organomet. Chem., 1983, vol. 250, p. 1.
Dzhemilev, U.M., D’yakonov, V.A., Khafizova, L.O., and Ibragimov, A.G., Tetrahedron, 2004, vol. 60, p. 1287.
Grossman, R.B. and Buchwald, S.L., J. Org. Chem., 1992, vol. 57, p. 5803.
Ojima, I., Tzamarioudaki, M., Li, Z., and Donovan, R.J., Chem. Rev., 1996, vol. 96, p. 635.
Ioffe, S.T. and Nesmeyanov, A.N., Metody elemento-organicheskoi khimii. Podgruppa magniya, berilliya, kal’tsiya, strontsiya, bariya (Methods of Organometallic Chemistry. Magnesium, Berillium, Calcium, Strontium, and Barium Subgroup), Moscow: Akad. Nauk SSSR, 1963.
Nesmeyanov, A.N., Nikitina, G.V., Nogina, O.V., Brainina, E.M., Posynskii, A.A., Magomedov, G.K.-N., Ioganson, A.A., Anisimov, K.N., Kolobova, I.E., Valueva, Z.P., Vyazankin, I.S., Shchelokov, R.N., Kruglaya, O.A., and Bolotova, G.T., Metody elemento-organicheskoi khimii. Podgruppa medi, skandiya, titana, vanadiya, khroma, margantsa. Lantanoidy i aktinoidy (Methods of Organometallic Chemistry. Copper, Scandium, Titanium, Vanadium, Chromium, and Manganese Subgroup. Lanthanides and Actinides), Moscow: Nauka, 1974.
Ibragimov, A.G., Khafizova, L.O., Satenov, K.G., Khalilov, L.M., Yakovleva, L.G., Rusakov, S.V., and Dzhemilev, U.M., Izv. Ross. Akad. Nauk, Ser. Khim., 1999, p. 1594.
Muslukhov, R.R., Khalilov, L.M., Ibragimov, A.G., Zolotarev, A.P., and Dzhemilev, U.M., Izv. Ross. Akad. Nauk, Ser. Khim., 1992, p. 2742.
Ibragimov, A.G., Minsker, D.L., Berg, A.A., Shitikova, O.V., Lomakina, S.I., and Dzhemilev, U.M., Izv. Ross. Akad. Nauk, Ser. Khim., 1992, p. 2791.
Dzhemilev, U.M., Ibragimov, A.G., Zolotarev, A.P., Muslukhov, R.R., and Tolstikov, G.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1989, p. 207.
Dzhemilev, U.M., Ibragimov, A.G., Zolotarev, A.P., Muslukhov, R.R., and Tolstikov, G.A., Izv. Akad. Nauk SSSR, Ser. Khim., 1990, p. 2831.
Ibragimov, A.G., Zagrebel’naya, I.V., Satenov, K.G., Khalilov, L.M., and Dzhemilev, U.M., Izv. Ross. Akad. Nauk, Ser. Khim., 1998, p. 712.
Author information
Authors and Affiliations
Additional information
__________
Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 3, 2005, pp. 363–368.
Original Russian Text Copyright © 2005 by Dzhemilev, D’yakonov, Khafizova, Ibragimov.
Rights and permissions
About this article
Cite this article
Dzhemilev, U.M., D’yakonov, V.A., Khafizova, L.O. et al. Cyclomagnesation of Olefins with Ethylmagnesium Bromide in the Presence of Titanium Complexes. Russ J Org Chem 41, 352–357 (2005). https://doi.org/10.1007/s11178-005-0169-z
Received:
Issue Date:
DOI: https://doi.org/10.1007/s11178-005-0169-z