Catalysis of the Michael reaction by iron(III): Calculations, mechanistic insights and experimental consequences

Journal of Organometallic Chemistry

Volumn 684, Issue 1-2, 2003, Pages 308-314

  Pelzer, Silke ^a   Kauf, Thomas ^b   van Wüllen, Christoph ^a   Christoffers, Jens ^b  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Chloride; DFT calculations; Iron; Iron complexes; Metal catalysis; Michael addition

Indexed keywords

ACRYLIC ACID DERIVATIVE; ANION; CARBON; ESTER; IRON COMPLEX; KETONE DERIVATIVE; LIGAND; METHYL GROUP; VINYL DERIVATIVE; WATER;

ARTICLE; CALCULATION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; CONTROLLED STUDY; EXPERIMENTATION; MICHAEL ADDITION; MOLECULAR MECHANICS; MOLECULAR STABILITY; REACTION ANALYSIS; SURFACE PROPERTY;

EID: 0142120418     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(03)00765-4     Document Type: Article

References (26)

1. Reviews: E.D. Bergmann, D. Ginsburg, R. Pappo, Org. React. 10 1959 179-555
2. D.A. Oare, C.H. Heathcock, in: E.L. Eliel, S.H. Wilen (Eds.), Topics in Stereochemistry, vol. 19, Wiley Interscience, New York, 1989, pp. 227-407
3. P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series vol. 9, Pergamon, Oxford, 1992.
4. Review: Christoffers J. Eur. J. Org. Chem. 1998 1259
5. Review: Christoffers J. Synlett 2001 723
6. Christoffers J. Chem. Commun. 1997 943
7. Christoffers J. J. Chem. Soc. Perkin Trans. 1 1997 3141
8. Christoffers J. Oertling H. Önal N. J. Prakt. Chem. 342 2000 546
9. Christoffers J. Tetrahedron Lett. 39 1998 7083
10. Christoffers J. Oertling H. Tetrahedron 56 2000 1339
11. Christoffers J. Oertling H. Leitner M. Synlett 2000 349
12. References cited in: Gmelins Handbuch der Anorganischen Chemie, Eisen, vol. 59 B, Verlag Chemie, Berlin, 1932, pp. 554-560.
13. Kocovsky P. Dvorak D. Tetrahedron Lett. 27 1986 5015
14. Kocovsky P. Dvorak D. Collect. Czech. Chem. Commun. 53 1988 2667
15. Gumbel G. Elias H. Inorg. Chim. Acta 342 2003 97
16. Gallo V. Mastrorilli P. Nobile C.F. Romanazzi G. Suranna P.G. J. Chem. Soc. Dalton Trans. 2002 4339
17. Kobayashi S. Kakumoto K. Sugiura M. Org. Lett. 4 2002 1319
18. Christoffers J. Org. Synth. 78 2000 249
19. v. Arnim M. Ahlrichs R. J. Comp. Chem. 19 1998 1746
20. Ahlrichs R. Bär M. Häser M. Horn H. Kölmel C. Chem. Phys. Lett. 162 1989 165
21. Treulter O. Ahlrichs R. J. Chem. Phys. 102 1995 346
22. Schäfer A. Huber C. Ahlrichs R. J. Chem. Phys. 100 1994 5829
23. 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, P. Salvador, J.J. Dannenberg, 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, J.A. Pople, Gaussian 98 (Revision A.1x), Gaussian, Inc., Pittsburgh, USA, 2001.
24. Becke A.D. Phys. Rev. A 38 1988 3098
25. Becke A.D. J. Chem. Phys. 98 1993 5648
26. Lee C. Yang W. Parr R.G. Phys. Rev. B 37 1988 785