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For excellent reviews, see the following: (a) Kharasch, M. S.; Reinmuth, O. Grignard Reactions of Nonmetallic Substances; Prentice-Hall: New York, 1954. (b) Niitzel, K. In Methoden der Organishen Chemie; (Houben-Weyl) Georg Thime Verlag: Stuttgart, 1973; Vol. XIII-2a, p 49. (c) Ashby, E. C. Q. Rev., Chem. Soc. 1967, 21, 259. (d) Thayer, J. S. Adv. Organomet. Chem. 1975, 13, 1. (e) Stowell, J. C. Carbanion in Organic Synthesis; Wiley: New York, 1979. (f) Negishi, E. Organometallics in Organic Synthesis; Wiley: New York, 1980; Vol. 1. (g) Lai, Y.-H. Synthesis 1981, 585. (h) Wakefield, B. J. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, 1982, Vol. 7, Chapter 44.
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Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. (b) Imamoto, T.; Sugiura, Y.; Takiyama, N. Tetrahedron Lett. 1984, 25, 4233. (c) Imamoto, T.; Kusumoto, T.; Yokoyama, M. J. Chem. Soc., Chem. Commun. 1982, 1042. (d) Imamoto, T.; Kusumoto, T.; Sugiura, Y.; Suzuki, N.; Takiyama, N. J. Chem. Soc. Jpn. 1985, 445. (e) Imamoto, T.; Sugiura, Y. J. Organomet. Chem. 1985, 285, C21. (f) Imamoto, T.; Sugiura, Y. J. Phy. Org. Chem. In press.
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Other research groups have recently employed organocerium reagents for the preparation of key intermediates to biologically active compounds (b) Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861. (c) Tamura, Y.; Sato, M.; Ohe, H.; Akai, A.; Kita, Y. Tetrahedron Lett. 1985, 26, 1549. (d) Nagasawa, K.; Kanbara, H.; Matsushita, K.; Ito, K. Tetrahedron Lett. 1985, 26, 6477. (e) Paquette, L. A.; Learn, K. S. J. Am. Chem. Soc. 1986, 108, 7873. (0 Paquette, L. A.; Learn, K. S.; Romine, J. L.; Lin, H.-S. J. Am. Chem. Soc. 1988, 110, 879. (g) Johnson, C. R.; Tait, B. D. J. Org. Chem. 1987, 52, 281. (h) Denmark, S. E.; Weber, T.; Piotrowski, J. Am. Chem. Soc. 1987, 107, 2224. (i) Guo, B. S.; Doubleday, W.; Cohen, T. J. Am. Chem. Soc. 1987, 109, 621. (j) Hart, D. J.; Huang, H.-C. J. Am. Chem. Soc. 1988, 110, 1634. (k) Corey, E. J.; Ha, D-C. Tetrahedron Lett. 1988, 29, 3171. (l) Robson, J. N.; Rowland, S. J. Tetrahedron Lett. 1988, 29, 3837
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Other research groups have recently employed organocerium reagents for the preparation of key intermediates to biologically active compounds. (a) Suzuki, M.; Kimura, Y.; Terashima, S. Chem. Lett. 1984, 1543. (b) Suzuki, K.; Ohkuma, T.; Tsuchihashi, G. Tetrahedron Lett. 1985, 26, 861. (c) Tamura, Y.; Sato, M.; Ohe, H.; Akai, A.; Kita, Y. Tetrahedron Lett. 1985, 26, 1549. (d) Nagasawa, K.; Kanbara, H.; Matsushita, K.; Ito, K. Tetrahedron Lett. 1985, 26, 6477. (e) Paquette, L. A.; Learn, K. S. J. Am. Chem. Soc. 1986, 108, 7873. (0 Paquette, L. A.; Learn, K. S.; Romine, J. L.; Lin, H.-S. J. Am. Chem. Soc. 1988, 110, 879. (g) Johnson, C. R.; Tait, B. D. J. Org. Chem. 1987, 52, 281. (h) Denmark, S. E.; Weber, T.; Piotrowski, J. Am. Chem. Soc. 1987, 107, 2224. (i) Guo, B. S.; Doubleday, W.; Cohen, T. J. Am. Chem. Soc. 1987, 109, 621. (j) Hart, D. J.; Huang, H.-C. J. Am. Chem. Soc. 1988, 110, 1634. (k) Corey, E. J.; Ha, D-C. Tetrahedron Lett. 1988, 29, 3171. (l) Robson, J. N.; Rowland, S. J. Tetrahedron Lett. 1988, 29, 3837.
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Preliminary report
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Preliminary report: Imamoto, T.; Takiyama, N.; Nakamura, K. Tetrahedron Lett. 1985, 26, 4763.
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A recent report dealing with reduction of carbonyl compounds with tert-butyl Grignard reagent
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A recent report dealing with reduction of carbonyl compounds with tert-butyl Grignard reagent: Maruoka, K.; Itoh, T.; Sakurai, M.; Nonoshita, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 3588.
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A similar result was reported by Buchbauer
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A similar result was reported by Buchbauer. Buchbauer, G. Tetrahedron Lett. 1977, 7.
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Yokoo, K.; Yamanaka, Y.; Fukagawa, T.; Taniguchi, H.; Fujiwara, Y. Chem. Lett. 1983, 1301. (b) Sigalov, A. B.; Petrov, E. S.; Rybakova, L. F.; Beletskaya, I. P. Izv. Akad. Nauk. SSSR, Ser. Khim. 1983, 2615. (c) Schumann, H.; Müller, J.; Bruncks, N.; Lauke, H.; Pickardt, J. Organometallies 1984, 3, 69.
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For discussions of the coordination properties of lanthanoids, see Gschneider, K. A., Jr., Eyring, L., Eds.; North-Holland: Amsterdam (b) Moeller, T. In Comprehensive Inorganic Chemistry; Bailar, J. C., Emeléus, H. J., Nyholm, R. Eds.; Pergamon Press: Oxford, 1973, Vol. 4, pp 1–101
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For discussions of the coordination properties of lanthanoids, see: (a) Rueben, J. In Handbook on the Physics and Chemistry of Rare Earths; Gschneider, K. A., Jr., Eyring, L., Eds.; North-Holland: Amsterdam, 1979; Vol. 4, pp 515–552. (b) Moeller, T. In Comprehensive Inorganic Chemistry; Bailar, J. C., Emeléus, H. J., Nyholm, R. Eds.; Pergamon Press: Oxford, 1973, Vol. 4, pp 1–101.
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For representative reviews dealing with organic reactions with lanthanoids, see: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573. (b) Marks, T. J.; Ernst, F. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, G.; Abel, F. G. A. Eds.; Pergamon Press: Oxford, 1982; Vol. 3, p 173. (c) Schumann, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 474. (d) Evans, W. J. Polyhedron 1987, 6, 803. (e) Natale, N. R. Org. Prep. Proc. Int. 1983, 15, 389. (f) Long, J. R. Aldrichimica Acta 1985, 18, 87. (g) Imamoto, T. J. Syn. Org. Chem. Jpn. 1988, 46, 540.
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For representative reviews on mechanistic studies on the Grignard reaction of carbonyl compounds, see: (a) Ashby, E. C.; Laemmle, J. T.; Newmann, H. M. Acc. Chem. Res. 1974, 2, 272. (b) Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317. (c) Dagonneau, M. M. Bull. Soc. Chim. Fr. 1982, II, 269. (d) Ashby, E. C.; Laemmle, J. T. Chem. Rev. 1975, 75, 521. (e) Ashby, E. C. Pure Appl. Chem. 1980, 52, 545. (f) Okubo, M.; Maruyama, K. Kagaku (Kyoto), 1980, 35, 338, 467.
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Haley, T. J. In Handbook on the Physics and Chemistry of Rare Earths; Gschneider, K. A. Jr., Eyring, L.; Eds.; North-Holland: Amsterdam, 1979; Vol. 4, pp 553–585.
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We are grateful to Professor Liotta, who kindly informed us of the experimental procedure for the preparation of this compound
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Liotta, D. Private Communication. We are grateful to Professor Liotta, who kindly informed us of the experimental procedure for the preparation of this compound.
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Private Communication
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Liotta, D.1
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