Complexes with phosphorus analogues of imidazoyl carbenes: Unprecedented formation of phosphenium complexes by coordination induced P-Cl bond heterolysis

Journal of Organometallic Chemistry

Volumn 617-618, Issue , 2001, Pages 383-394

  Gudat, Dietrich ^a   Haghverdi, Asadollah ^a   Nieger, Martin ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Bond heterolysis; Carbene analogues; Metal ligand multiple bonding; Phosphenium complexes; Acceptor ligands

Indexed keywords

EID: 0001892562     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(00)00624-0     Document Type: Article

References (46)

1. Fischer E.O., Maasböl A. Angew. Chem. Int. Ed. Engl. 3:1964;580.
2. (a) K.H. Dotz, in: A. de Meijere, H. tom Dieck (Ed.), Organometallics in Organic Syntheses, Springer, Berlin, 1988.
3. (b) R.H. Grubbs, in: G. WIlkinson, F.G.A. Stone, E.W. Abel (Eds.), Comprehensive Organometallic Chemistry, vol. 8, Pergamon, Oxford, 1982, p. 499.
4. (c) W. Herrmann, C. Köcher, Angew. Chem. Int. Ed. Engl. 36 (1997) 2162.
5. Igau A., Grützmacher H., Baceiredo A., Bertrand G. J. Am. Chem. Soc. 110:1988;6463.
6. Arduengo A.J., Harlow R.L., Kline M. J. Am. Chem. Soc. 113:1991;361.
7. (a) G. Bertrand, R. Reed, Coord. Chem. Rev. 137 (1994) 323.
8. (b) A.J. Arduengo, Acc. Chem. Res. 32 (1999) 913.
9. (c) D. Bourissou, O. Guerret, F.P. Gabbai, G. Bertrand, Chem. Rev. 100 (2000) 39.
10. (a) (E=Si): M. Denk, R. Lennon, R. Hayashi, R. West, A.V. Belyakov, H.P. Verne, A. Haaland, M. Wagner, N. Metzler, J. Am. Chem. Soc. 116 (1994) 2691.
11. (b) B. Gehrhus, M.F. Lappert, J. Heinicke, R. Boese, D. Bläser, J. Chem. Soc. Chem. Commun. (1995) 1931.
12. (c) (E=Ge): W.A. Herrmann, M. Denk, J. Behm, W. Scherer, F.R. Klingan, H. Bock, B. Solouki, M. Wagner, Angew. Chem. 104 (1992) 1489; Angew. Chem. Int. Ed. Engl. 31(1992) 1485.
13. (c) (E=Ge): W.A. Herrmann, M. Denk, J. Behm, W. Scherer, F.R. Klingan, H. Bock, B. Solouki, M. Wagner, Angew. Chem. 104 (1992) 1489; Angew. Chem. Int. Ed. Engl. 31(1992) 1485.
14. -): E.S. Schmidt, A. Jockisch, H. Schmidbaur, J. Am. Chem. Soc. 121 (1999) 9758.
15. +): G. Boche, P. Andrews, K. Harms, M. Marsch, K.S. Rangappa, M. Schimeczek, C. Willeke, J. Am. Chem. Soc. 118 (1996) 4925.
16. +): I.A. Litvinov, V.A. Naumov, T.V. Gryaznova, A.N. Pudovik, A.M. Kibardin, Dokl. Akad. Nauk SSSR 312 (1990) 623.
17. +) M.K. Denk, S. Gupta, A.J. Lough, Eur. J. Inorg. Chem. (1999) 41.
18. +): C.J. Carmalt, V. Lomeli, B.G. McBurnett, A.H. Cowley, J. Chem. Soc. Chem. Commun. (1997) 2095.
19. (a) C. Heinemann, T. Müller, Y. Apeloig, H. Schwarz, J. Am. Chem. Soc. 118 (1996) 2023.
20. (b) C. Boehme, G. Frenking, J. Am. Chem. Soc. 118 (1996) 3039.
21. (a) D. Gudat, Eur. J. Inorg. Chem. (1998) 1087.
22. (b) M.K. Denk, S. Gupta, A.J. Lough, Eur. J. Inorg. Chem. (1999) 41.
23. (c) D. Gudat, A. Haghverdi, H. Hupfer, M. Nieger, Chem. Eur. J. (2000) 3414.
24. M. Denk, R.K. Hayashi, R. West, J. Chem. Soc. Chem. Commun. (1994) 33.
25. Gudat D., Holderberg A.W., Kotila S., Nieger M. Chem. Ber. 129:1996;465.
26. Gudat D. Coord. Chem. Rev. 173:1997;71.
27. (a) A.H. Cowley, R. Kemp, Chem. Rev. 85 (1985) 367.
28. (b) M. Sanchez, M.R. Mazières, L. Lamandé, R. Wolf, in: M. Regitz, O. Scherer (Eds.), Multiple Bonds and Low Coordination Chemistry in Phosphorus Chemistry, Georg Thieme Verlag, Stuttgart, 1990, p. 129.
29. (a) R.G. Montemayor, D.T. Sauer, S. Fleming, D.W. Bennett, M.G. Thomas, R.W. Parry, J. Am. Chem. Soc. 100 (1978) 2231.
30. (b) A.H. Cowley, R.A. Kemp, J.C. Wilburn, Inorg. Chem. 20 (1981) 4289.
31. Bennett D.W., Coffer J.L. J. Coord. Chem. 33:1994;271.
32. An analogous reactivity for 1 [OTf] and 8 was observed as well as for the 1,3-dimesityl-1,3,2-diazaphospholenium triflate and the corresponding p-chloro-compound which both lack the additional Cl substituent at the ring, however, due to the limited amount of available material the nature of the formed complexes was only elucidated by in situ NMR spectroscopic studies.
33. (a) H. Nakazawa, Y. Yamaguchi, K. Miyoshi, J. Organomet. Chem. 465 (1994) 193.
34. (b) H. Nakazawa, Y. Yamaguchi, T. Mizuta, K. Miyoshi, Organometallics 14 (1995) 4173.
35. D. Gudat, M. Nieger, E. Niecke, J. Chem. Soc. Dalton Trans. (1989) 693.
36. For recent reviews on the use of inverse detection NMR techniques for the characterisation of metal complexes see: For recent reviews on the use of inverse detection NMR techniques for the characterisation of metal complexes see: (a) D. Gudat, Ann. Rep. NMR Spect. 38 (1999) 139. (b) W.v. Philipsborn, Chem. Soc. Rev. 28 (1999) 95. (c) J. Mason (Ed.), Multinuclear NMR, Plenum, New York, 1987.
37. For recent reviews on the use of inverse detection NMR techniques for the characterisation of metal complexes see: (a) D. Gudat, Ann. Rep. NMR Spect. 38 (1999) 139. (b) W.v. Philipsborn, Chem. Soc. Rev. 28 (1999) 95. (c) J. Mason (Ed.), Multinuclear NMR, Plenum, New York, 1987.
38. For recent reviews on the use of inverse detection NMR techniques for the characterisation of metal complexes see: (a) D. Gudat, Ann. Rep. NMR Spect. 38 (1999) 139. (b) W.v. Philipsborn, Chem. Soc. Rev. 28 (1999) 95. (c) J. Mason (Ed.), Multinuclear NMR, Plenum, New York, 1987.
39. Nakazawa H., Yamaguchi Y., Miyoshi K., Nagasawa A. Organometallics. 15:1996;2517.
40. Tolman C.A. Chem. Rev. 77:1977;313.
41. Gudat D., Haghverdi A., Nieger M. Angew. Chem. Int. Ed. Engl. 39:2000;3084.
42. Since no structural data for the 1,3-dimethyl-1,3,2-diazaphospholidinium cation are available, the bonding parameters of the N-t-Bu substituted cation from Ref. [9b] were considered instead.
43. (a) Z. Zhou, R.G. Parr, J.F. Garst, Tetrahedron Lett. (1988) 4843.
44. (b) Z. Zhou, R.G. Parr, J. Am. Chem. Soc 111 (1989) 7371.
45. (a) G.M. Sheldrick, SHELXS-97, Acta Crystallogr. Sect. A 46 (1990) 467.
46. (b) G.M. Sheldrick, SHELXL-97, University of Göttingen, Germany, 1997.