Carbodiphosphoranes: The chemistry of divalent carbon(0)

Angewandte Chemie - International Edition

Volumn 45, Issue 47, 2006, Pages 8038-8042

  Tonner, Ralf ^a   Öxler, Florian ^a   Neumüller, Bernhard ^a   Petz, Wolfgang ^a   Frenking, Gernot ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Bonding analysis; Carbodiphosphoranes; Carbon; Cations; Donor acceptor systems

Indexed keywords

CARBON; POSITIVE IONS; SYNTHESIS (CHEMICAL);

BONDING ANALYSIS; BONDING MODEL; CARBODIPHOSPHORANES; DONOR ACCEPTOR SYSTEMS;

PHOSPHORUS COMPOUNDS;

EID: 33845506629     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602552     Document Type: Article

References (52)

1. A. J. Arduengo III, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 2801.
2. a) A. Baceiredo, G. Bertrand, G. Sicard, J. Am. Chem. Soc. 1985, 107, 4781;
3. b) A. Igau, H. Grützmacher, A. Baceiredo, G. Bertrand, J. Am. Chem. Soc. 1988, 110, 6463;
4. c) A. Igau, A. Baceiredo, G. Trinquier, G. Bertrand, Angew. Chem. 1989, 101, 617;
5. Angew. Chem. Int. Ed. Engl. 1989, 28, 621.
6. a) W. Kirmse, Angew. Chem. 2004, 116, 1799;
7. Angew. Chem. Int. Ed. 2004, 43, 1767;
8. b) Carbene Chemistry (Ed.: G. Bertrand), Marcel Dekker, New York, 2002.
9. a) S. Marrot, T. Kato, H. Gornitzka, A. Baceiredo, Angew. Chem. 2006, 118, 2660;
10. Angew. Chem. Int. Ed. 2006, 45, 2598;
11. b) the first cyclic CDP was reported in: U. Schubert, C. Kappenstein, B. Milewski-Mahrla, H. Schmidbaur, Chem. Ber. 1981, 114, 3070.
12. a) F. Ramirez, N. B. Desai, B. Hansen, N. McKelvie, J. Am. Chem. Soc. 1961, 83, 3539;
13. b) G. E. Hardy, J. I. Zink, W. C. Kaska, J. C. Baldwin, J. Am. Chem. Soc. 1978, 100, 8002.
14. Recent reviews: a) N. D. Jones, R. G. Cavell, J. Organomet. Chem. 2005, 690, 5485;
15. b) O. I. Kolodiazhnyi, Phosphorous Ylides: Chemistry and Application in Organic Synthesis, Wiley-VCH, Weinheim, 1999;
16. c) O. I. Kolodiazhnyi, Tetrahedron 1996, 52, 1855;
17. d) Ylides and Imines of Phosphorus (Ed.: A. W. Johnson), Wiley, New York, 1993.
18. a) W. C. Kaska, D. K. Mitchell, R. F. Reichelderfer, J. Organomet. Chem. 1973, 47, 391;
19. b) W. C. Kaska, K. A. O. Starzewski, Ylides and Imines of Phosphorus (Ed.: A. W. Johnson), Wiley, New York, 1993, p. 485.
20. a) P. von R. Schleyer, A. J. Kos, Tetrahedron 1983, 39, 1141;
21. b) H. Grützmacher, C. M. Marchand, Coord. Chem. Rev. 1997, 163, 287.
22. D. G. Gilheany, Chem. Rev. 1994, 94, 1339.
23. [33] The full set of calculated geometries and energies is given in the Supporting Information.
24. A. M. Magill, K. J. Cavell, B. F. Yates, J. Am. Chem. Soc. 2004, 126, 8717.
25. B. Kovacevic, Z. B. Maksic, Org. Lett. 2001, 3, 1523.
26. a) J. D. Walker, R. Poli, Polyhedron 1989, 8, 1293;
27. b) W. P. Jensen, H. Gehrke, D. R. Jones, I.-H. Suh, R. A. Jacobson, Z. Kristallogr. 1996, 211, 829.
28. a) W. Petz, C. Kutschera, S. Tschan, F. Weller, B. Neumüller, Z. Anorg. Allg. Chem. 2003, 629, 1235-1244;
29. b) W. Petz, F. Weller, Z. Kristallogr. 1997, 212, 157;
30. c) A. Schmidtpeter, F. Zwaschka, W. S. Sheldrick, Chem. Ber. 1985, 118, 1078;
31. d) P. J. Carroll, D. D. Titus, J. Chem. Soc. Dalton Trans. 1977, 824.
32. F. Öxler, Diploma thesis, Marburg, 2006.
33. 2): δ = 23.6 ppm.
34. 2) contains 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.
35. A. J. Arduengo, III, H. V. R. Dias, J. C. Calabrese, F. Davidson, Organometallics 1993, 12, 3405.
36. P. K. Hurlburt, J. J. Rack, S. F. Dec, O. P. Anderson, S. H. Strauss, Inorg. Chem. 1993, 32, 373.
37. I. Romeo, M. Bardají, M. C. Gimeno, M. Laguna, Polyhedron 2000, 19, 1837.
38. R. F. W. Bader, Atoms in Molecules: A Quantum Theory, Oxford University Press, Oxford, 1990.
39. H. Schmidbaur, Chem. Soc. Rev. 1995, 24, 391.
40. J. Vicente, A. R. Singhal, P. G. Jones, Organometallics 2002, 21, 5887.
41. J. J. Daly, P. Wheatley, J. Chem. Soc. A 1966, 1703.
42. J. Koput, Chem. Phys. Lett. 2000, 320, 237.
43. T. Kappe, E. Ziegler, Angew. Chem. 1974, 86, 529;
44. Angew. Chem. Int. Ed. Engl. 1974, 13, 491.
45. Gaussian 03 (Revision D.01): M. J. Frisch et al., see the Supporting Information.
46. R. Ahlrichs, M. Baer, M. Haeser, H. Horn, C. Koelmel, Chem. Phys. Lett. 1989, 162, 165.
47. A. D. Becke, Phys. Rev. A 1988, 38, 3098;
48. J. P. Perdew, Phys. Rev. B 1986, 33, 8822.
49. A. Schaefer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571.
50. F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297.
51. K. Eichkorn, O. Treutler, H. Ohm, M. Häser, R. Ahlrichs, Chem. Phys. Lett. 1995, 242, 652.
52. D. Andrae, U. Häussermann, M. Dolg, H. Stoll, H. Preuss, Theor. Chim. Acta 1990, 77, 123.