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Volumn 34, Issue 6, 2005, Pages 760-761

The chemistry of alkylstrontium halide analogues: Barbier-type alkylation of imines with alkyl halides

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EID: 23944465433     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.760     Document Type: Article
Times cited : (21)

References (31)
  • 1
    • 84942797082 scopus 로고
    • Magnesium, Calcium, Strontium and Barium
    • ed. by G. Wilkinson, F. G. A. Stone, and E. W. Abel, Pergamon Press, Oxford, Chap. 3 and 4, respectively
    • 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.
    • (1982) Comprehensive Organometallic Chemistry , vol.1 , pp. 121
    • Bell, N.A.1    Lindsell, W.E.2
  • 2
    • 0002337893 scopus 로고
    • Beryllium Magnesium, Calcium, Strontium and Barium
    • ed. by E. W. Abel, F. G. A. Stone, and G. Wilkinson, Pergamon Press, Oxford, Chap. 3, and references cited therein
    • 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.
    • (1995) Comprehensive Organometallic Chemistry II , vol.1 , pp. 57
    • Lindsell, W.E.1
  • 4
    • 23944482547 scopus 로고    scopus 로고
    • Product 5, 6, 7 and 9
    • for Beryllium, Magnesium, Calcium and Barium, respectively
    • and see also "Product 5, 6, 7 and 9" in "Science of Synthesis" Vol. 7 for Beryllium, Magnesium, Calcium and Barium, respectively.
    • Science of Synthesis , vol.7
  • 11
    • 23544455576 scopus 로고
    • 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).
    • (1975) J. Organomet. Chem. , vol.101
    • Gowenlock, G.1    Lindsell, W.E.2    Singh, B.3
  • 18
  • 19
    • 0000716787 scopus 로고
    • Nucleophilic Addition to Imines and Imine Derivatives
    • ed. by B. M. Trost and I. Fleming, Pergamon Press, Oxford, Chap. 1.12, and references cited therein
    • 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.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 355-396
    • Volkmann, R.A.1
  • 21
    • 0036407530 scopus 로고    scopus 로고
    • 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.
    • Chem. Commun. , vol.2002 , pp. 2440
    • Huang, T.1    Keh, C.C.K.2    Li, C.-J.3
  • 23
    • 23944520975 scopus 로고    scopus 로고
    • note
    • The reaction also proceeded in DMF or DMSO, but THF gave the best result.
  • 24
    • 23944478508 scopus 로고    scopus 로고
    • note
    • 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.
  • 25
    • 23944500941 scopus 로고    scopus 로고
    • note
    • Using excess amount of alkyl iodide other than methyl iodide, the C,N-dialkylated product was obtained in very low yield.
  • 31
    • 23944471260 scopus 로고    scopus 로고
    • note
    • 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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