Unusual redox properties of a sterically hindered water-soluble chromium porphyrin. Electrochemical and spectral speciation

(Note: The full text of this document is currently only available in the PDF Version )

Yu-Hui Lu and Y. Oliver Su


Abstract

meso-Tetrakis(3-sulfonatomesityl)porphyrinato]chro-mium( III) [CrIII(tsmp)] in aqueous solution can undergo electrochemical reduction to form a stable radical anion and oxidation to generate very stable radical cations CrIII(tsmp.+) and O[double bond, length as m-dash]CrIV(tsmp.+), which reacts with alkenes to produce enones at room temperature.


References

  1. Catalytic Activation of Dioxygen by Metal Complexes, ed. L. I. Simandi, Kluwer, Dordrecht, 1992 Search PubMed.
  2. Metalloporphyrins in Catalytic Oxidations, ed. R. A. Sheldon, Marcel Dekker, New York, 1994 Search PubMed.
  3. B. Meunier, Chem. Rev., 1992, 92, 1411 CrossRef CAS; J. Muzart, Chem. Rev., 1992, 92, 113 CrossRef CAS.
  4. O. Bortolini and B. Meunier, J. Chem. Soc., Chem. Commun., 1983, 1364 RSC.
  5. P. Battioni, J.-P. Renaud, J. F. Bartoli and D. Mansuy, J. Chem. Soc., Chem. Commun., 1986, 341 RSC; P. L. Anelli, S. Banfi, F. Legramandi, F. Montanari, G. Pozzi and S. Quici, J. Chem. Soc., Perkin Trans. 1, 1993, 1345 RSC.
  6. L.-C. Yuan and T. C. Bruice, J. Am. Chem. Soc., 1986, 108, 1643 CrossRef CAS; R. D. Arasasingham, S. Jeon and T. T. Bruice, J. Am. Chem. Soc., 1992, 114, 2536 CrossRef CAS.
  7. J. T. Groves and M. Stern, J. Am. Chem. Soc., 1988, 110, 8628 CrossRef CAS.
  8. J. T. Groves and Y. Watanabe, J. Am. Chem. Soc., 1988, 110, 8443 CrossRef CAS.
  9. J. Bernadou, A.-S. Fabiano, A. Robert and B. Meunier, J. Am. Chem. Soc., 1994, 116, 9375 CrossRef CAS.
  10. W.-H. Wong, D. Ostovic and T. C. Bruice, J. Am. Chem. Soc., 1987, 109, 3428 CrossRef CAS.
  11. (a) M. H. Liu and Y. O. Su, J. Chem. Soc., Chem. Commun., 1994, 971 RSC; (b) M. H. Liu, C. Y. Yeh and Y. O. Su, Chem. Commun., 1996, 1437 RSC; (c) T.-S. Lee and Y. O. Su, J. Electroanal. Chem., 1996, 414, 69 CrossRef CAS; (d) M. H. Liu and Y. O. Su, J. Electroanal. Chem., 1997, in the press Search PubMed.
  12. S. E. Creager and R. W. Murray, Inorg. Chem., 1985, 24, 3824 CrossRef CAS; S. E. Creager, S. A. Rayback and R. W. Murray, J. Am. Chem. Soc., 1986, 108, 4225 CrossRef CAS; J. T. Groves, Z. Gross and M. Stern, Inorg. Chem., 1994, 33, 5065 CrossRef CAS.
  13. D. J. Liston, B. J. Kennedy, K. S. Murray and B. O. West, Inorg. Chem., 1985, 24, 1561 CrossRef CAS; D. J. Liston and B. O. West, Inorg. Chem., 1985, 24, 1568 CrossRef CAS.
  14. K. R. Ashley, J. G. Leipoldt and V. K. Joshi, Inorg. Chem., 1980, 19, 1608 CrossRef CAS; J. G. Leipoldt, S. S. Basson and D. R. Rabie, J. Inorg. Nucl. Chem., 1981, 43, 3239 CrossRef CAS; K. R. Ashley and J. Kuo, Inorg. Chem., 1988, 27, 3556 CrossRef CAS.
  15. S.-M. Chen and Y. O. Su, J. Chem. Soc., Chem. Commun., 1990, 491 RSC.
  16. Y. O. Su, D. Kim and T. G. Spiro, J. Electroanal. Chem., 1988, 246, 363 CrossRef CAS.
  17. Electrochemical Methods. Fundamentals and Applications, ed. A. J. Bard and L. R. Faulkner, Wiley, New York, 1980 Search PubMed.
  18. W. A. Lee, L.-C. Yuan and T. C. Bruice, J. Am. Chem. Soc., 1988, 110, 4277 CrossRef CAS; J. M. Garrison and T. C. Bruice, J. Am. Chem. Soc., 1989, 111, 191 CrossRef CAS; S. Jeon and T. C. Bruice, Inorg. Chem., 1991, 30, 4311 CrossRef CAS; 1992, 31, 4843.
  19. J. W. Buchler, K. L. Lay, L. Castle and V. Ullrich, Inorg. Chem., 1982, 21, 842 CrossRef CAS.
  20. D. M. Guldi, P. Hambright, D. Lexa, P. Neta and J.-M. Savéant, J. Phys. Chem., 1992, 96, 4459 CrossRef CAS; D. M. Guldi and P. Neta, J. Chem. Soc., Faraday Trans., 1992, 88, 2013; 2337 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.