Strained, stable 2-Aza-1-phosphabicyclo[n.1.0]alkane and -alkene Fe(CO)4complexes with dynamic phosphinidene behavior

Chemistry - A European Journal

Volumn 11, Issue 12, 2005, Pages 3631-3642

  Borst, Mark L G ^a   Van Riet, Niels Der ^a   Lemmens, Renske H ^a   De Kanter, Franciscus J J ^a   Schakel, Marins ^a   Ehlers, Andreas W ^a   Mills, Allison M ^b   Lutz, Martin ^b   Spek, Anthony L ^b   Lammertsma, Koop ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Iron; Phosphinidenes; Phosphorus heterocycles; Small ring systems

Indexed keywords

ADDITION REACTIONS; CHELATION; CHEMICAL BONDS; COMPLEXATION; PHOSPHORUS COMPOUNDS; PROTONS;

BICYCLIC COMPLEXES; HETEROCYCLES; IONIC PATH; PHOSPHINIDENE;

PARAFFINS;

ALKENE; HETEROCYCLIC COMPOUND; IRON DERIVATIVE; ORGANOMETALLIC COMPOUND; PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STANDARD; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKENES; AZA COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; IRON COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHOSPHINES; REFERENCE STANDARDS;

EID: 20444484882     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200401249     Document Type: Article

References (50)

1. K. D. Dillon, F. Mathey, J. F. Nixon, Phosphorus: The Carbon Copy, Wiley, Chichester, 1998.
2. X. Li, S. I. Weissman, T.-S. Lin, P. P. Gaspar, A. H. Cowley, A. I. Smirnov, J. Am. Chem. Soc. 1994, 116, 7899-7900.
3. For recent reviews: a) K. Lammertsma, Top. Curr. Chem. 2003, 229, 95-119;
4. b) K. Lammertsma, M.J.M. Vlaar, Eur. J. Org. Chem., 2002, 1127-1138;
5. c) F. Mathey, N. H. Tran Huy, A. Marinetti, Helv. Chim. Acta 2001, 84, 2938-2957.
6. For examples; a) P. B. Hitchcock, M. F. Lappert, W.-P. Leung, J. Chem. Soc. Chem. Commun.1987, 1282-1283;
7. b) J. Ho, R. Rousseau, D. W. Stephan, Organometallics 1994, 13, 1918-1926;
8. c) C. C. Cummins, R. R. Schrock, W. M. Davis, Angew. Chem. 1993, 105, 758-761;
9. Angew. Chem. Int. Ed. Engl. 1993, 32, 756-759;
10. d) J. S. Freundlich, R. R. Schrock, W. M. Davis, J. Am. Chem. Soc. 1996, 118, 3643-3655;
11. e) R. Melenkivitz, D.J, Mindiola, G. L. Hillhouse, J. Am. Chem. Soc. 2002, 124, 3846-3847;
12. f) A. T. Termaten, T. Nijbacker, M. Schakel, M. Lutz, A. L. Spek, K. Lammertsma, Organometallics 2002, 21, 3196-3202;
13. g) A. T. Termaten, M. Schakel, A. W. Ehlers, M. Lutz, A. L. Spek, K. Lammertsma, Chem. Eur. J. 2003, 9, 3577-3582;
14. h) R. Waterman, G. L. Hillhouse, J. Am. Chem. Soc. 2003, 125, 13350-13351;
15. i) F. Basuli, B.C. Bailey, J. C. Huffman, M. H. Baik, D. J. Mindiola, J. Am. Chem. Soc. 2004, 126, 1924-1925.
16. a) A. Marinetti, F. Mathey, J. Fischer, A. Mitschier, J. Am. Chem. Soc. 1982, 104, 4484-4485;
17. b) A. Marinetti, F. Mathey, Organometallics 1982, 1, 1488-1492.
18. a) F. Mercier, B. Deschamps, F. Mathey, J. Am. Chem. Soc. 1989, 111, 9098-9100;
19. b) A. Marinetti, L. Ricard, F. Mathey, Synthesis 1992, 157-162.
20. a) R. Streubel, Top. Curr. Chem. 2003, 223, 91-109;
21. b) R. Streubel, A. Kusenberg, J. Jeske, P. G. Jones, Angew. Chem. 1994, 106, 2564-2566;
22. Angew. Chem. Int. Ed. Engl. 1994, 33, 2427-2429.
23. a) J. B. M. Wit, G. T. van Eijkel, F. J. J. de Kanter, M. Schakel, A. W. Ehlers, M. Lutz, A. L. Spek, K. Lammertsma, Angew. Chem. 1999, 111, 2716-2719;
24. Angew. Chem. Int. Ed. 1999, 38, 2596-2599;
25. b) J. B. M. Wit, G. T. van Eijkel, F. J. J. de Kanter, M. Schakel, A. W. Ehlers, M. Lutz, A. L. Spek, K. Lammertsma, Tetrahedron 2000, 56, 137-141.
26. J. B. M. Wit, Ph.D. thesis, Vrije Universiteit, Amsterdam (The Netherlands), 2001.
27. R. B. King, F. J. Wu, E. M. Holt, J. Am. Chem. Soc. 1987, 109, 7764-7775.
28. 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, 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.3), Gaussian, Inc., Pittsburgh, Pennsylvania, USA, 1998.
29. -3. CCDC-256107 (7b), 256108 (17a), and 256109 (19) 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.
30. A. R. Rossi, R. Hoffmann, Inorg. Chem. 1975, 14, 365-374.
31. H. Brombach, E. Niecke, M. Nieger, Organometallics 1991, 10, 3949-3951.
32. F. Mathey, Chem. Rev. 1990, 90, 997-1025.
33. T. Morikawa, H. Sasaki, R. Hanai, A. Shibuya, T. Taguchi, J. Org. Chem. 1994, 59, 97-103.
34. T. G. Driver, K. A. Woerpel, J. Am. Chem. Soc. 2003, 125, 10659-10663.
35. J. Svara, A. Marinetti, F. Mathey, Organometallics 1986, 5, 1161-1167.
36. A. Marinetti, F. Mathey, J. Fischer, A. Mitschler, Nouv. J. Chim. 1984, 8, 453-457.
37. I. K. Boessenkool, J. C. A. Boeyens, J. Cryst. Mol. Struct. 1980, 10, 11-18.
38. J. K. Crandall, W. J. Michaely, J. Org. Chem. 1984, 49, 4244-4248.
39. a) Y. Li, T. J. Marks, J. Am. Chem. Soc. 1996, 118, 706-707 (synthesis);
40. b) T. E. Müller, K.-A. Pleier, J. Chem. Soc. Dalton Trans. 1999, 583-587 (NMR spectroscopy).
41. a) L. Brandsma, Preparative Acetylenic Chemistry, 1988, 2nd Ed., Elsevier, Amsterdam, pp. 256-257 and pp. 250-251;
42. b) M. S. Baird, A. G. W. Baxter, A. Hoorfar, I. Jefferies, J. Chem. Soc. Perkin Trans. 1 1991, 2575-2581.
43. J.-M. Surzur, P. Tordo, L. Stella, Bull Soc. Chim. Fr. 1970, 111-114.
44. R. G. Finke, T. N. Sorrell, Org. Synth. 1988, 807-813.
45. a) J. Stonehouse, P. Adell, J. Keeler, A. J. Shaka, J. Am. Chem. Soc. 1994, 116, 6037-6038;
46. b) K. Stott, J. Stonehouse, J. Keeler, T.-L. Hwang, A. J. Shaka, J. Am. Chem. Soc. 1995, 117, 4199-4200.
47. See also: M. J. S. Dewar, R. Jones, J. Am. Chem. Soc. 1968, 90, 2137-2144.
48. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smits, C. Smykalla, The DIRDIF99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen (The Netherlands), 1999.
49. G. M. Sheldrick, SHELXL-97. Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
50. A. L. Spek, J. Appl. Crystallogr. 2003, 36, 7-13.