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Volumn 351, Issue 3, 2009, Pages 353-356

An unusual peroxide-mediated amination of cycloalkanes with nitroarenes

Author keywords

Amination; Cycloalkanes; Nitroarenes; Peroxides

Indexed keywords


EID: 60849103093     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800689     Document Type: Article
Times cited : (29)

References (36)
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    • A. S. Goldman, K. I. Goldberg, in: Activation and Functionalization of C-H Bonds, (Eds. : K. I. Goldberg, A. S. Goldman), ACS Symposium Series 885, American Chemical Society, Washington, DC, 2004, pp 1-43;
    • g) A. S. Goldman, K. I. Goldberg, in: Activation and Functionalization of C-H Bonds, (Eds. : K. I. Goldberg, A. S. Goldman), ACS Symposium Series 885, American Chemical Society, Washington, DC, 2004, pp 1-43;
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    • For recent representative examples on alkane functionalization, see: a
    • For recent representative examples on alkane functionalization, see: a) J. Y. K. Tsang, M. S. A. Buschhaus, P. Legzdins, J. Am. Chem. Soc. 2007, 129, 5372;
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 5372
    • Tsang, J.Y.K.1    Buschhaus, M.S.A.2    Legzdins, P.3
  • 21
    • 33846286096 scopus 로고    scopus 로고
    • and references cited therein. For reductive amination of aldehydes and ketones, see
    • For reductive amination of aldehydes and ketones, see: M. J. Bhanushali, N. S. Nandurkar, M. D. Bhor, B. M. Bhanage, Tetrahedron Lett. 2007, 48,1273, and references cited therein.
    • (2007) Tetrahedron Lett , vol.48 , pp. 1273
    • Bhanushali, M.J.1    Nandurkar, N.S.2    Bhor, M.D.3    Bhanage, B.M.4
  • 22
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    • For other representative amination methods involving the cycloalkyl group, see, a
    • For other representative amination methods involving the cycloalkyl group, see : a) D. Hollmann, S. Bähn, A. Tillack, M. Beller, Angew. Chem. 2007, 119, 8440;
    • (2007) Angew. Chem , vol.119 , pp. 8440
    • Hollmann, D.1    Bähn, S.2    Tillack, A.3    Beller, M.4
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    • For successful direct amination of alkanes via nitrene, see: C. G. Liang, F. Collet, F. Robert-Peillard, P. Müller, R. H. Dodd, P. Dauban, J. Am. Chem. Soc. 2008, 130, 343.
    • For successful direct amination of alkanes via nitrene, see: C. G. Liang, F. Collet, F. Robert-Peillard, P. Müller, R. H. Dodd, P. Dauban, J. Am. Chem. Soc. 2008, 130, 343.
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    • for a review on the CDC reactions, see: C.-J. Li, Acc. Chem. Res. ASAP, DOI: 10.1021/ar800164n.
    • e) for a review on the CDC reactions, see: C.-J. Li, Acc. Chem. Res. ASAP, DOI: 10.1021/ar800164n.
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    • Nitrosobenzene and aniline also reacted with cyclooctane under similar conditions and gave the same product 4a in 51% and 28% yield, respectively. Surprisingly, old bottles of reagents gave better yields of the desired product than new ones and purified ones. The reason is not clear
    • Nitrosobenzene and aniline also reacted with cyclooctane under similar conditions and gave the same product 4a in 51% and 28% yield, respectively. Surprisingly, old bottles of reagents gave better yields of the desired product than new ones and purified ones. The reason is not clear.


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