Rhenium(I) di- and tri-carbonyl compounds of polypyridyl-like ligands: electrochemical reactions of fac-[Re(CO)₃(dpk)Cl] (dpk = di-2-pyridyl ketone) with electrophiles and Group I and II metal ions

Abstract

In contrast to the facile formation of fac-[Re(CO)₃(dpk)Cl] 1 from the reaction between [Re(CO)₅Cl] and dpk [(C₅H₄N)₂C(O)], in refluxing toluene, [Re(CO)₅Cl] was recovered unchanged when di-2-pyridylamine, dpa [(C₅H₄N)₂NH], was allowed to react with [Re(CO)₅Cl] under a variety of conditions. However, a mixture of [Re(CO)₅Cl] and PPh₃ in refluxing toluene followed by a CH₂Cl₂ solution of dpa gave cis-[Re(CO)₂(PPh₃)(dpa)Cl]. The intermediate involved appears to be a general synthon for the binding of the Re^I(CO)₂(PPh₃)Cl chromophore to a variety of bi- and mono-dentate nitrogen-donor ligands and has been utilized to isolate cis-[Re(CO)₂(PPh₃)(dpk)Cl]. Nucleophilic addition of water at the carbonylic carbon atom of co-ordinated dpk in 1 and cis-[Re(CO)₂(PPh₃)(dpk)Cl] resulted in the hydration of the keto group and formation of fac-[Re(CO)₃{(C₅H₄N)₂C(O)(OH)}] and cis-[Re(CO)₂(PPh₃){(C₅H₄N)₂C(O)(OH)}]. The compounds isolated exhibit rich electrochemical and photochemical properties and the potential application of fac-[Re(CO)₃(dpk)Cl] as an electrochemical sensor for electrophiles and Group I and II metal ions is demonstrated.

References

1. X.-M. Wang, H.-S. Sun and X.-Z. You, Polyhedron, 1996, 15, 3543.
2. V. Levacher and C. Moberg, J. Org. Chem., 1995, 60, 1755.
3. H. Nishiyama, S. Yamaguchi, S.-B. Park and K. Itoh, Tetrahedron: Asymmerty, 1993, 4, 143.
4. S. Itsuno, M. Nakano, K. Ito, A. Hirao, M. Owa, N. Kanda and S. Nakahama, J. Chem. Soc., Perkin Trans. 1, 1985, 2615.
5. V. A. Davankov, J. D. Navratil and H. F. Walton, Ligand Exchange Chromatography, CRC Press, Boca Raton, FL, 1988.
6. C. Moberg, T. Norin, L. Rakos and K. Sjodin, J. Chromatogr., 1991, 585, 309.
7. D. E. Morris, Y. Ohsawa, D. P. Segers, M. K. DeArmond and K. W. Hank, Inorg. Chem., 1984, 23, 3010.
8. W. J. Holland and J. Bozic, Anal. Chem., 1968, 40, 433.
9. A. Basu, A. R. Saple and N. Y. Sapre, J. Chem. Soc., Dalton Trans., 1987, 1797.
10. A. Basu, T. G. Kasar and N. Y. Sapre, Inorg. Chem., 1988, 27, 4539.
11. M. C. Feller and R. Robson, Aust. J. Chem., 1968, 21, 2919.
12. M. C. Feller and R. Robson, Aust. J. Chem., 1970, 23, 1997.
13. J. D. Ortego, D. D. Waters and C. S. Steele, J. Inorg. Nucl. Chem., 1974, 36, 751.
14. S. O. Sommerer, J. D. Baker, W. P. Jensen, A. Hamza and R. A. Jacobson, Inorg. Chim. Acta, 1993, 210, 173.
15. J. D. Ortego and D. L. Perry, J. Inorg. Nucl. Chem., 1973, 35, 3031.
16. B. E. Fisher and H. Sigel, J. Inorg. Nucl. Chem., 1975, 37, 2127.
17. T. I. A. Gerber, H. J. Kemp, J. G. H. Du Preez and G. Bandoli, J. Coord. Chem., 1993, 28, 329.
18. T. I. A. Gerber, J. Bruwer, G. Bandoli, J. Perils and J. G. H. Du Preez, J. Chem. Soc., Dalton Trans., 1995, 2189.
19. A. J. Blake, S. Parsons, J. M. Rawson and R. E. P. Winpenny, Polyhedron, 1995, 14, 1895.
20. M. R. Kratz and D. G. Hendricker, Polymer, 1986, 27, 1641.
21. M. Bakir and B. P. Sullivan, J. Chem. Soc., Dalton Trans., 1995, 1733.
22. M. Bakir, S. Paulson, P. Goodson and B. P. Sullivan, Inorg. Chem., 1992, 31, 1127.
23. G. A. Neyhart, M. Bakir, J. Boaz, W. J. Vining and B. P. Sullivan, Coord. Chem. Rev., 1991, 111, 27.
24. G. Tapolsky, R. Duesing and T. J. Meyer, Inorg. Chem., 1990, 29, 2285.
25. R. Lin, Y. Fu, C. P. Brock and T. F. Guarr, Inorg. Chem., 1992, 31, 4346.
26. M. S. Wrighton and D. L. Morse, J. Am. Chem. Soc., 1974, 96, 998.
27. B. D. Rossenaar, D. T. Stufkens and A. Vlcek, Jr., Inorg. Chem., 1996, 35, 2902.
28. V. D. J. Stufkens, Coord. Chem. Rev., 1990, 104, 39.
29. B. P. Sullivan, C. M. Bolinger, D. Conrad, W. J. Vining and T. J. Meyer, J. Chem. Soc., Chem. Commun., 1985, 1414.
30. K. Yang, S. G. Bott and M. G. Richmond, Organometallics, 1995, 14, 2387.
31. N. B. Thornton and K. S. Schanze, Inorg. Chem., 1993, 32, 4994.
32. J. C. Vites and M. M. Lynam, Coord. Chem. Rev., 1995, 142, 1.
33. G. J. Stor, F. Hartl, J. W. M. van Outersterp and D. J. Stufkens, Organometallics, 1995, 14, 1115.
34. V. W.-W. Yam, K. K.-W. Lo, K.-K. Cheung and R. Y.-C. Kong, J. Chem. Soc., Chem. Commun., 1995, 1191.
35. M. Bakir and J. A. M. McKenzie, J. Electroanal. Chem., 1997, 425, 621.
36. C. Bianchini, A. Marchi, L. Marvelli, M. Peruzzini, A. Romerosa, R. Rossi and A. Vacca, Organometallics, 1995, 14, 3203.
37. M. Bakir, unpublished work.
38. J. V. Casper, B. P. Sullivan and T. J. Meyer, Inorg. Chem., 1984, 23, 2104.
39. F. Hartl and A. Vlcek, Jr., Inorg. Chem., 1992, 31, 2869.
40. P. Zanello, A. Cinquantini, F. Laschi, R. Rossi, A. Duatti, A. Marchi and L. Magon, Polyhedron, 1988, 7, 195.
41. H. B. Abrahamson and M. S. Wrighton, Inorg. Chem., 1987, 17, 3385.
42. D. M. Manuta and A. J. Less, Inorg. Chem., 1983, 22, 3825.
43. R. W. Taft and M. J. Kamlet, Inorg. Chem., 1983, 22, 250.
44. A. J. Less, Chem. Rev., 1987, 87, 711.
45. F. L. Minn, C. L. Trichilo, C. R. Hurt and N. Filipescu, J. Am. Chem. Soc., 1970, 92, 3600.
46. O. Ishitani, C. Pac and H. Sakurai, J. Org. Chem., 1983, 48, 2941.
47. S. M. Fredericks and M. S. Wrighton, J. Am. Chem. Soc., 1980, 102, 6166.
48. J. Armand, C. Bellec, L. Boulares and J. Pinson, J. Org. Chem., 1983, 48, 2847.
49. P. D. Beer and K. Y. Wild, Polyhedron, 1996, 15, 775.
50. P. D. Beer, Chem. Soc. Rev., 1989, 18, 4; Adv. Inorg. Chem., 1992, 39, 79.
51. P. D. Beer, S. W. Dent, N. C. Fletcher and T. J. Wear, Polyhedron, 1996, 15, 2983.