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Volumn , Issue 26, 2008, Pages 4466-4474

Reactivity of (Mono-tert-butyloxiranyl)lithium: A theoretical ab initio study

Author keywords

Ab initio calculations; Alkyllithium; Carbenes; Oxiranyl anion; Reaction mechanisms

Indexed keywords


EID: 53849134164     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800457     Document Type: Article
Times cited : (6)

References (57)
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    • However, other strong bases (or mixture of bases) may be used, see: A. Mordini, D. Peruzzi, F. Russo, M. Valacchi, G. Reginato, A. Brandi, Tetrahedron 2005, 61, 3349-3360.
    • However, other strong bases (or mixture of bases) may be used, see: A. Mordini, D. Peruzzi, F. Russo, M. Valacchi, G. Reginato, A. Brandi, Tetrahedron 2005, 61, 3349-3360.
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    • see also an addition to a Fischer carbene complex: V. Capriati, S. Florio, R. Luisi, F. M. Perna, J. Barluenga, J. Org. Chem. 2005, 70, 5852-5858.
    • see also an addition to a Fischer carbene complex: V. Capriati, S. Florio, R. Luisi, F. M. Perna, J. Barluenga, J. Org. Chem. 2005, 70, 5852-5858.
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    • In this oxiranyl species, no C-H insertion is possible. This is observed in the (1,2-di-tBu-oxiranyl)lithium. Work on this species is in progress and will be submitted later for publication.
    • In this oxiranyl species, no C-H insertion is possible. This is observed in the (1,2-di-tBu-oxiranyl)lithium. Work on this species is in progress and will be submitted later for publication.
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    • 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
    • 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 03, Revision B.04, Gaussian, Inc., Pittsburgh, PA, 2003.
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    • 1. The resulting reaction path is identical to that leading to Pr1.
    • 1. The resulting reaction path is identical to that leading to Pr1.
  • 56
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    • 3COLi) with one MeLi molecule give a similar geometry: A planar LiOCLi lozenge is found (O-Li = 1.79 Å; C-Li = 2.15 Å), and the stabilisation energy is 56.0 kcal/mol.
    • 3COLi) with one MeLi molecule give a similar geometry: A planar LiOCLi lozenge is found (O-Li = 1.79 Å; C-Li = 2.15 Å), and the stabilisation energy is 56.0 kcal/mol.


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