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Volumn 13, Issue 23, 2007, Pages 6745-6754

Hypervalent iodine-mediated aziridination of alkenes: Mechanistic insights and requirements for catalysis

Author keywords

Aziridines; Hypervalent compounds; Iodine; Oxidation; Reaction mechanism

Indexed keywords

AMINES; CATALYSIS; IODINE; OXIDATION; THERMAL EFFECTS;

EID: 34547770310     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700306     Document Type: Article
Times cited : (90)

References (71)
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    • For the first example of an enantioselective oxidation catalysed by enantiopure iodoarenes see
    • For the first example of an enantioselective oxidation catalysed by enantiopure iodoarenes see: R. D. Richardson, T. K. Page, S. Altermann, S. M. Paradine, A. N. French, T. Wirth, Synlett 2007, 528-532.
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    • Richardson, R.D.1    Page, T.K.2    Altermann, S.3    Paradine, S.M.4    French, A.N.5    Wirth, T.6
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    • Mixing alkenes with (diacetoxyiodo)benzene in dichloromethane at room temperature does not result in the 1,2-diacetoxyalkane. This is in contrast to the reaction when other ligands are used on the iodane (see reference [20])
    • Mixing alkenes with (diacetoxyiodo)benzene in dichloromethane at room temperature does not result in the 1,2-diacetoxyalkane. This is in contrast to the reaction when other ligands are used on the iodane (see reference [20])
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    • Calculations performed by using Gaussian 98 (Revision A.9) M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, 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, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian, Inc, Pittsburgh PA, 1998;
    • a) Calculations performed by using Gaussian 98 (Revision A.9) M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, 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, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998;
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    • LANL2DZ(d,p) basis set was obtained from the Extensible Computational Chemistry Environment Basis Set Database, Version 02/02/ 06, as developed and distributed by the Molecular Science Computing Facility, Environmental and Molecular Sciences Laboratory which is part of the Pacific Northwest Laboratory, P. O. Box 999, Richland, Washington 99352 (USA) and funded by the US Department of Energy. The Pacific Northwest Laboratory is a multi-program laboratory operated by Battelle Memorial Institute for the US Department of Energy under contract DE-AC06-76RLO 1830. Contact Karen Schuchardt for further information. The LANL2DZ-(d,p) basis set was first described by: P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299-310;
    • LANL2DZ(d,p) basis set was obtained from the Extensible Computational Chemistry Environment Basis Set Database, Version 02/02/ 06, as developed and distributed by the Molecular Science Computing Facility, Environmental and Molecular Sciences Laboratory which is part of the Pacific Northwest Laboratory, P. O. Box 999, Richland, Washington 99352 (USA) and funded by the US Department of Energy. The Pacific Northwest Laboratory is a multi-program laboratory operated by Battelle Memorial Institute for the US Department of Energy under contract DE-AC06-76RLO 1830. Contact Karen Schuchardt for further information. The LANL2DZ-(d,p) basis set was first described by: P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299-310;
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    • diffuse and polarisation functions taken from: C. E. Check, T. O. Faust, J. M. Bailey, B. J. Wright, T. M. Gilbert, L. S. Sunderlin, J. Phys. Chem. A 2001, 105, 8111-8116.
    • diffuse and polarisation functions taken from: C. E. Check, T. O. Faust, J. M. Bailey, B. J. Wright, T. M. Gilbert, L. S. Sunderlin, J. Phys. Chem. A 2001, 105, 8111-8116.
  • 61
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    • PCM solvation model used as implemented in Gaussian 98.
    • PCM solvation model used as implemented in Gaussian 98.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.