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1
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84942797082
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Magnesium, Calcium, Strontium and Barium
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ed. by G. Wilkinson, F. G. A. Stone, and E. W. Abel, Pergamon Press, Oxford, Chap. 3 and 4, respectively
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a) N. A. Bell, "Beryllium," and W. E. Lindsell, "Magnesium, Calcium, Strontium and Barium," in "Comprehensive Organometallic Chemistry," ed. by G. Wilkinson, F. G. A. Stone, and E. W. Abel, Pergamon Press, Oxford (1982), Vol. 1, Chap. 3 and 4, p 121 and p 155, respectively.
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Comprehensive Organometallic Chemistry
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Bell, N.A.1
Lindsell, W.E.2
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2
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0002337893
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Beryllium Magnesium, Calcium, Strontium and Barium
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ed. by E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon Press, Oxford, Chap. 3, and references cited therein
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b) W. E. Lindsell, "Beryllium Magnesium, Calcium, Strontium and Barium," in "Comprehensive Organometallic Chemistry II," ed. by E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon Press, Oxford (1995), Vol. 1, Chap. 3, p 57, and references cited therein.
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Comprehensive Organometallic Chemistry II
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Lindsell, W.E.1
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3
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23944465045
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Product Class 8: Strontium Compounds
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ed. by H. Yamamoto, Thieme, Stuttgart
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c) N. Miyoshi, "Product Class 8: Strontium Compounds," in "Houben-Weyl: Methods of Molecular Transformation, Science of Synthesis," ed. by H. Yamamoto, Thieme, Stuttgart (2004), Vol. 7, p 685,
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Houben-Weyl: Methods of Molecular Transformation, Science of Synthesis
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Miyoshi, N.1
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4
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23944482547
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Product 5, 6, 7 and 9
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for Beryllium, Magnesium, Calcium and Barium, respectively
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and see also "Product 5, 6, 7 and 9" in "Science of Synthesis" Vol. 7 for Beryllium, Magnesium, Calcium and Barium, respectively.
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Science of Synthesis
, vol.7
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5
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1542355987
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For the synthesis of alkylcalcium halide and the reaction using Rieke calcium, see: a) K. Mochida, S. Ogura, and T. Yamanishi, Bull. Chem. Soc. Jpn., 59, 2633 (1986).
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Bull. Chem. Soc. Jpn.
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Mochida, K.1
Ogura, S.2
Yamanishi, T.3
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6
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0000718158
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b) T. Wu, H. Xiong, and R. D. Rieke, J. Org. Chem., 55, 5045 (1990).
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J. Org. Chem.
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Wu, T.1
Xiong, H.2
Rieke, R.D.3
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7
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0000420582
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c) R. A. O'Brien, T. Chen, and R. B. Rieke, J. Org. Chem., 57, 2667 (1992).
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O'Brien, R.A.1
Chen, T.2
Rieke, R.B.3
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8
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84992534721
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For the reaction using Rieke barium, see: d) A. Yanagisawa, S. Habaue, and H. Yamamoto, J. Am. Chem. Soc., 113, 8955 (1991).
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Yanagisawa, A.1
Habaue, S.2
Yamamoto, H.3
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9
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0000058830
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e) A. Yanagisawa, S. Habaue, K. Yasue, and H. Yamamoto, J. Am. Chem. Soc., 116, 6130 (1994).
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Yanagisawa, A.1
Habaue, S.2
Yasue, K.3
Yamamoto, H.4
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11
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23544455576
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Lindsell et al. reported that alkylstrontium halides reacted with carbonyl compounds to afford the corresponding products in low yields, with the exception of the reaction with benzophenone. a) G. Gowenlock, W. E. Lindsell, and B. Singh, J. Organomet. Chem., 101, C37 (1975).
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J. Organomet. Chem.
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Gowenlock, G.1
Lindsell, W.E.2
Singh, B.3
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12
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37049113486
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b) G. Gowenlock, W. E. Lindsell, and B. Singh, J. Chem. Soc., Dalton Trans., 1978, 657.
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J. Chem. Soc., Dalton Trans.
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Gowenlock, G.1
Lindsell, W.E.2
Singh, B.3
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14
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1542266084
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b) L. N. Cherkasov, V. I. Panov, and V. N. Cherkasov, Russ. J. Org. Chem., 29, 411 (1993).
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Russ. J. Org. Chem.
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Cherkasov, L.N.1
Panov, V.I.2
Cherkasov, V.N.3
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17
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1542290076
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N. Miyoshi, K. Kamiura, H. Oka, A. Kita, R. Kuwata, D. Ikehara, and M. Wada, Bull. Chem. Soc. Jpn., 77, 341 (2004).
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Miyoshi, N.1
Kamiura, K.2
Oka, H.3
Kita, A.4
Kuwata, R.5
Ikehara, D.6
Wada, M.7
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18
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0038106171
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a) R. Bloch, Chem. Rev., 98, 1407 (1998).
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Chem. Rev.
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Bloch, R.1
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19
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0000716787
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Nucleophilic Addition to Imines and Imine Derivatives
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ed. by B. M. Trost and I. Fleming, Pergamon Press, Oxford, Chap. 1.12, and references cited therein
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b) R. A. Volkmann, "Nucleophilic Addition to Imines and Imine Derivatives," in "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, Chap. 1.12, pp 355-396, and references cited therein.
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Volkmann, R.A.1
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0000366717
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M. Wada, Y. Sakurai, and K. Akiba, Tetrahedron Lett., 25, 1079 (1984).
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Wada, M.1
Sakurai, Y.2
Akiba, K.3
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21
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0036407530
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Recently there have been a few reports on zinc-promoted alkylation reactions of aldimines with simple alkyl halides. a) T. Huang, C. C. K. Keh, and C.-J. Li, Chem. Commun., 2002, 2440.
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Chem. Commun.
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Huang, T.1
Keh, C.C.K.2
Li, C.-J.3
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22
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0346392147
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b) T. Iwai, T. Ito, T. Mizuno, and Y. Ishino, Tetrahedron Lett., 45, 1083 (2004).
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Iwai, T.1
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Ishino, Y.4
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23
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23944520975
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note
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The reaction also proceeded in DMF or DMSO, but THF gave the best result.
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24
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23944478508
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note
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Commercially available metallic strontium ingot in liquid paraffin was cut into small pieces using a sharp knife in preparation for the start of each reaction.
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25
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23944500941
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note
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Using excess amount of alkyl iodide other than methyl iodide, the C,N-dialkylated product was obtained in very low yield.
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27
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0000984857
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b) B. L. Emling, R. J. Horvath, A. J. Saraceno, E. F. Ellermeyer, L. Haile, and L. D. Hudac, J. Org. Chem., 24, 657 (1959).
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J. Org. Chem.
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Emling, B.L.1
Horvath, R.J.2
Saraceno, A.J.3
Ellermeyer, E.F.4
Haile, L.5
Hudac, L.D.6
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31
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23944471260
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note
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4. After evaporation of the solvent, the residue was purified by column chromatography on aluminum oxide (hexane:ethyl acetate = 20:1-4:1) to give the corresponding alkylated product, N-(1-phenylpentyl)aniline (218 mg, 95% yield) as a colorless oil.
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