Reactions of organic disulfides and gold(I) complexes

Metal-Based Drugs

Volumn 6, Issue 4-5, 1999, Pages 247-253

  DiLorenzo, Melanie ^a   Ganesh, Shantheni ^a   Tadayon, Lily ^a   Chen, Jinhua ^a   Bruce, Mitchell R M ^a   Bruce, Alice E ^a  

^a University of Maine   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; GOLD COMPLEX; PROTON;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; ELECTROCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0032730005     PISSN: 07930291     EISSN: None     Source Type: Journal    
DOI: 10.1155/MBD.1999.247     Document Type: Article

References (39)

1. Puddephatt, R. J. The Chemistry of Gold, Elsevier, NY, (1978).
2. (a) Hill, D. T.; Lantos, I.; Sutton, B. M. U.S. Patent 4,114,642, Sept. 19, 1978.
3. (b) Reglinksi, J.; Smith, W. E. Inorg. Chim. Acta, 152, 261-264 (1988).
4. (c) Wang, S.; Fackler, J. P., Jr. Inorg. Chem. 29, 4404-4407 (1990).
5. (d) Hofreiter, S.; Paul, M.; Schmidbaur, H. Chem. Ber., 128, 901-905 (1995).
6. (e) Roberts, J. R.; Xiao, J.; Schliesman, B.; Parsons, D. J.; Shaw, C. F., III Inorg. Chem. 35, 424-433 (1996).
7. (f) Xiao, J.; Shaw, C. F., III Inorg. Chem., 31, 3706-3710 (1992).
8. For several leading references concerning metal thiolate-disulfide interchange see: (a) Dean, P. A. W.; Jagadese, J. Inorg. Chem., 25, 514-519 (1986)
9. (b) Zhu, Z.; Petering, D. H.; Shaw, C. F, III Inorg. Chem. 34, 4477-4483 (1995).
10. Foley, J.; Fort, R.C., Jr.; McDougal, K.; Bruce, M.R.M.; Bruce, A.E. Metal-Based Drugs, 1, 405-417 (1994).
11. Ganesh, S. "Reactions of Gold(I) Phosphine Thiolate Complexes with Organic Disulfides" University of Maine, M.S. Thesis, 1995.
12. (a) Fava, A.; Reichenbach, G.; Peron, U. J. Am. Chem. Soc., 89, 6696-6700 (1967).
13. (b) Oswald, A. A.; Wallace, T. J. Organic Sulfur Compounds; Vol. II, Pergamon Press, Ltd.: London, 1966.
14. (c) Kosower, E. M. in Glutathione: Chemical, Biochemical and Medical Aspects, Part A; Dolphin, D.; Arramovic, O.; Eds.; Wiley-Interscience: New York, 1989, Chapter 4.
15. (d) Lees, W. J.; Whitesides, G. M. J. Org. Chem. 58, 642-647 (1993) and references therein.
16. (e) Sungh, R.; Whitesides, G. M. J. Am. Chem. Soc., 112, 6304-6309 (1990).
17. (f) Houk, J.; Whitesides, G. M. Tetrahedon, 45, 91 (1989).
18. (g) Houk, J.; Whitesides, G. M. J. Am. Chem. Soc., 109, 6825-6836 (1987).
19. (h) Kice, J. L.; Slebocka-Tilk, H. J. Am. Chem. Soc., 104 7123-7130 (1984).
20. (a) Oae, S. Organic Chemistry of Sulfur, Plenum Press, NY, (1997).
21. (b) Mukaiyama, T.; Takahashi, K. Tet. Lett., 56, 5907-5908 (1968).
22. Narayanaswamy, R.; Young, M.A.; Parkhurst, E.; Ouellette, M.; Kerr, M.E.; Ho, D.; Elder, R.C.; Bruce, A.E.; Bruce, M.R.M. Inorg. Chem., 32, 2506-2517 (1993).
23. Dean, J. Analytical Chemistry Handbook, McGraw Hill, 133-135 (1995).
24. Dilorenzo, M. "Gold(I) Mediated Thiolate/Disulfide Exchange Reactions" University of Maine, M.S. Thesis, 1995.
25. DiLorenzo, M.; Ganesh, S.; Tadayon, L.; Chen, J.; Bruce, M. R. M.; Bruce, A. E. unpublished results.
26. 4Cl, for a total of 16 experiments.
27. 6] can be used as a reference electrolyte in the concentration range under investigation.
28. Foley, J. B.; Gay, S. E.; Turmel, C.; Wei, G.; Jiang, T.; Narayanaswamy, R.; Foxman, B. M.; Vela, M. J.; Bruce, A. E.; Bruce, M. R. M. Metal-Based Drugs, submitted.
29. B. Andrieux, C. P.; Hapiot, P.; Pinson, J.; Saveant, J.-M. J. Am. Chem. Soc., 115, 7783-7788 (1993).
30. Wilker, J. J.; Lippard, S. J. J. Am. Chem. Soc., 117, 8682-8683 (1995).
31. (a) Hormann, A. L.; Shaw, C. F., III; Bennett, D. W.; Reiff, W. M. Inorg. Chem., 25, 3953-3957 (1986).
32. (b) Hormann-Arendt, A. L.; Shaw, C. F., III Inorg. Chem., 29, 4683-4687 (1990).
33. For an example of deprotonation of dppm coordinated to gold(I) see Fernandez, E. J.; Gimeno, M. C.; Jones, P. G.; Laguna, A.; Laguna, M.; Lopez-de-Luzuriaga, J. M. Organometallics, 14, 2918-2922 (1995).
34. (a) Harwell, D. E.; Mortimer, M. D.; Knobler, C. B.; Anet, F. A. L.; Hawthorne, M. F. J. Am. Chem. Soc., 118, 2678-2685 (1996).
35. (b) Schmidbaur, H. Gold Bull., 23, 11-20 (1990).
36. Assefa, Z.; McBurnett, B. G.; Staples, R. J.; Fackler, J. P., Jr.; Assmann, B.; Angermaier, K.; Schmidbaur, H. Inorg. Chem., 34, 75-83 (1995).
37. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. C. Principles and Applications of Organotransition Metal Chemistry, University Science Books,: Mill Valley, CA, 1987.
38. Fackler, J. P., Jr. Polyhedron, 16, 1-17 (1997).
39. Dyadchenko, V. Russ. Chem. Rev., 51, 265-271 (1982).