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Ytterbium: a) Y. Taniguchi, K. Takaki, and Y. Fujiwara, Rev. Heteroatom Chem., 12, 163 (1995) and Ref. 1i and references cited therein. samarium: b) R. Yanada, K. Bessho, and K. Yanada, Chem. Lett., 1994, 1279. c) R. Yanada, K. Bessho, and K. Yanada, Synlett, 1995, 443. d) R. Yanada, N. Negoro, K. Bessho, and K. Yanada, Synlett, 1995, 1261. e) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 37, 9313 (1996). f) R. Yanada, N. Negoro, K. Yanada, and T. Fujita, Tetrahedron Lett., 38, 3271 (1997). g) Z.-B. Ding and S.-H. Wu, Youji Huaxue, 17, 165 (1997). h) L. Wang and Y. Zhang, Tetrahedron, 54, 11129 (1998). i) S. Talukdar and J.-M. Fang, J. Org. Chem. 66, 330 (2001). cerium: j) T. Imamoto, T. Kusumoto, Y. Hatanaka, and M. Yokoyama, Tetrahedron Lett., 23, 1353 (1982). k) S. Fukuzawa, T. Fujinami, and S. Sakai, J. Chem. Soc., Chem. Commun., 1986, 475. l) S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai, J. Org. Chem., 55, 1628 (1990).
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3SiI equivalent and used as a versatile reagent for the conversion of alcohols into organoiodide compounds. See: a) G. A. Olah, S. C. Narang, B. G. B. Gupta, and R. Malhotra, J. Org. Chem., 44, 1247 (1979). b) T. Sakai, K. Miyata, M. Utaka, and A. Takeda, Tetrahedron Lett., 28, 3817 (1987). c) T. Sakai, K. Miyata, S. Tsuboi, A. Takeda, M. Utaka, and S. Torii, Bull. Chem. Soc. Jpn., 62, 3537 (1989). d) S. Irifune, T. Kibayashi, Y. Ishii, and M. Ogawa, Synthesis, 1988, 366. e) T. Kanai, S. Irifune, Y. Ishii, and M. Ogawa, Synthesis, 1989, 283.
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When 5 was added to the solution, in which copper(I) iodide was treated with 1/3 molar amount of lanthanum metal, the reductive dimerization was not accelerated. On the basis of the result, the reaction pathway including the formation of lanthanum-copper-combined active reducing species cannot be ruled out at the present time.
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49
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85038471448
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Various highly reactive metals have been prepared and used for various reactions. See: Ref. 13 and references cited therein.
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50
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On the iodination of alcohols with chlorotrimethylsilane/sodium iodide reagent, it was reported that the reaction of benzylic or allylic alcohols was faster than that of aliphatic alcohols. See: Ref. 12a
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51
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85038477238
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In the case of primary and secondary aliphatic alcohols, lanthanum metal was completely consumed even if no coupling reaction proceeded.
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