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Volumn 13, Issue 11, 2007, Pages 3113-3119

Mechanistic study on rearrangement cascades starting from annulated 2-Aza-hepta-2,4-dienyl-6-ynyl anions: Formation of aniline and azepine derivatives

Author keywords

Azepines; Density functional calculations; Lithium; Organic chemistry; Ring closure; Zinc compounds

Indexed keywords

AMIDES; ANILINE; DENSITY FUNCTIONAL THEORY; LITHIUM COMPOUNDS; REACTION KINETICS; X RAY DIFFRACTION; ZINC COMPOUNDS;

EID: 34250669473     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601491     Document Type: Article
Times cited : (19)

References (24)
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    • Gaussian 03, Revision C.01. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. C
    • Gaussian 03, Revision C.01. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004. Details of the quantum chemical calculations may be obtained from E.-U. Würthwein upon request.
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    • Data sets were collected with Nonius KappaCCD diffractometers, in case of Mo-radiation equipped with rotating anode generator. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326),
    • Data sets were collected with Nonius KappaCCD diffractometers, in case of Mo-radiation equipped with rotating anode generator. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326),
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    • absorption correction SORTAV (R. H. Blessing
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    • and Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. Sect. A 2003, 59, 228-234),
    • and Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. Sect. A 2003, 59, 228-234),
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    • structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473),
    • structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473),
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    • structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göltingen, 1997). CCDC-620 928 (12), -620929 (19a), and 620 930 (20) 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/
    • structure refinement SHELXL-97 (G. M. Sheldrick, Universität Göltingen, 1997). CCDC-620 928 (12), -620929 (19a), and 620 930 (20) 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/
  • 24


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