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Volumn , Issue 21, 2005, Pages 4654-4662

The intramolecular aromatic electrophilic substitution of aminocyclopropanes prepared by the Kulinkovich-de Meijere reaction

Author keywords

Amides; Aromatic substitution; Cyclisation; Cyclopropanes; Titanium

Indexed keywords


EID: 27644479596     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500428     Document Type: Article
Times cited : (39)

References (53)
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    • Bringmann, G.1    Ewers, C.L.J.2    Walter, R.3
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    • [5e]
    • [5e].
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    • note
    • 13C NMR spectrum, a peak at δ = 133.9 ppm could be assigned as the α carbon of the enamine.
  • 30
    • 27644552378 scopus 로고    scopus 로고
    • note
    • The types of argon available in our institute are "Arcal 1" and "Nertal" (Air Liquide), normally used for arc welding and plasma cutting applications.
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    • 27644562385 scopus 로고    scopus 로고
    • note
    • 13C NMR analysis. Therefore, their formation cannot be explained by oxidation during column chromatography.
  • 34
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    • It has been established that five-membered ring cyclic enamines are generally more basic and more reactive towards electrophiles than their six-membered homologues: a) A. G. Cook, M. L. Absi, V. K. Bowden, J. Org. Chem. 1995, 60, 3169-3171;
    • (1995) J. Org. Chem. , vol.60 , pp. 3169-3171
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    • b) B. Kempf, N. Hampel, A. R. Ofial, H. Mayr, Chem. Eur. J. 2003, 9, 2209-2218. It should be noted, however, that unlike our intermediates, the cyclic enamines studied in these references do not include the nitrogen atom in the same ring as the carbon-carbon double bond.
    • (2003) Chem. Eur. J. , vol.9 , pp. 2209-2218
    • Kempf, B.1    Hampel, N.2    Ofial, A.R.3    Mayr, H.4
  • 36
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    • AM1 calculations (M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909) were performed with the MOPAC 97 program (Fujitsu Limited: 1993-1997) in the CS Chem. 3D® Pro system (CambridgeSoft Corporation, Cambridge, U. S. A.).
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902-3909
    • Dewar, M.J.S.1    Zoebisch, E.G.2    Healy, E.F.3    Stewart, J.J.P.4
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    • note
    • 1H NMR spectra is shown in the supporting information; for supporting information see also the footnote on the first page of this article
  • 39
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    • note
    • Only a trace amount of acid would be sufficient since a proton is released after the cyclisation during the re-aromatisation step.
  • 41
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    • a of the cyclic iminium ion should lie in the range 10-12; b) R. L. Hinman, Tetrahedron 1968, 24, 185-190.
    • (1968) Tetrahedron , vol.24 , pp. 185-190
    • Hinman, R.L.1
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    • note
    • [4].
  • 49
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    • note
    • Experimental details about the preparation of this compound can be found in the supporting information.
  • 50
    • 27644459175 scopus 로고    scopus 로고
    • note
    • The structure and characterisation of this compound can be found in the supporting information.
  • 51
    • 27644452811 scopus 로고    scopus 로고
    • CCDC-273312, -273313, and -273314 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.