View PDF Version
 
DOI: 10.1039/A809876J (Paper) Reference Section for: Chem. Commun., 1999, 387-388

Use of 2-methyl-1-phenylpropan-2-yl hydroperoxide (MPPH) as a mechanistic probe for the heterolytic versus homolytic O–O bond cleavage of tert-alkyl hydroperoxide by iron(III) porphyrin complex

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

Wonwoo Nam, Hye J. Choi, Hui J. Han, So H. Cho, Ha J. Lee and So-Yeop Han

Abstract

The mechanism of the O–O bond cleavage of tert-alkyl hydroperoxide by iron(III) porphyrin complexes has been studied using 2-methyl-1-phenylpropan-2-yl hydroperoxide (MPPH) as a mechanistic probe; the hydroperoxide O–O bond is cleaved both heterolytically and homolytically and partitioning between the two pathways significantly depends on the reaction conditions such as the pH of the reaction solutions and the nature of porphyrin and axial ligands.

References

  1. M. Sono, M. P. Roach, E. D. Coulter and J. H. Dawson, Chem. Rev., 1996, 96, 2841 CrossRef CAS; T. G. Traylor and P. S. Traylor, in Active Oxygen in Biochemistry, ed. J. S. Valentine, C. S. Foote, A. Greenberg and J. F. Liebman, Blackie Academic and Professional, Chapman and Hall, London, 1995, pp. 84–187 Search PubMed; B. Meunier, Chem. Rev., 1992, 92, 1411 Search PubMed.
  2. T. G. Traylor, C. Kim, W.-P. Fann and C. L. Perrin, Tetrahedron, 1998, 54, 7977 CrossRef CAS and refs. therein.
  3. O. Almarsson and T. C. Bruice, J. Am. Chem. Soc., 1995, 117, 4533 CrossRef CAS and refs. therein.
  4. (a) F. Minisci, F. Fontana, S. Araneo, F. Recupero, S. Banfi and S. Quici, J. Am. Chem. Soc., 1995, 117, 226 CrossRef CAS; (b) S. E. J. Bell, P. R. Cooke, P. Inchley, D. R. Leanord, J. R. Lindsay Smith and A. Robbins, J. Chem. Soc., Perkin Trans. 2, 1991, 549 RSC; (c) R. Labeque and L. J. Marnett, J. Am. Chem. Soc., 1989, 111, 6621 CrossRef CAS.
  5. P. A. MacFaul, D. D. M. Wayner and K. U. Ingold, Acc. Chem. Res., 1998, 31, 159 CrossRef CAS; P. A. MacFaul, K. U. Ingold, D. D. M. Wayner and L. Que, Jr., J. Am. Chem. Soc., 1997, 119, 10 594 CrossRef CAS; P. A. MacFaul, I. W. C. E. Arends, K. U. Ingold and D. D. M. Wayner, J. Chem. Soc., Perkin Trans. 2, 1997, 135 RSC; I. W. C. E. Arends, K. U. Ingold and D. D. M. Wayner, J. Am. Chem. Soc., 1995, 117, 4710 CrossRef CAS.
  6. G.-X. He and T. C. Bruice, J. Am. Chem. Soc., 1991, 113, 2747 CrossRef CAS; A. J. Castellino and T. C. Bruice, J. Am. Chem. Soc., 1988, 110, 158 CrossRef.
  7. J. T. Groves, Z. Gross and M. K. Stern, Inorg. Chem., 1994, 33, 5065 CrossRef CAS.
  8. A. Hadasch, A. Sorokin, A. Rabion and B. Meunier, New J. Chem., 1998, 45 RSC; R. Song, A. Sorokin, J. Bernadou and B. Meunier, J. Org. Chem., 1997, 62, 673 CrossRef CAS; S. M. S. Chauhan, P. P. Mohapatra, B. Kalra, T. S. Kohli and S. Satapathy, J. Mol. Catal. A: Chem., 1996, 113, 239 CrossRef CAS.
  9. S. J. Yang and W. Nam, Inorg. Chem., 1998, 37, 606 CrossRef CAS and refs. therein.
  10. Y. J. Lee, Y. M. Goh, S.-Y. Han, C. Kim and W. Nam, Chem. Lett., 1998, 837 CrossRef CAS; T. G. Traylor, C. Kim, J. L. Richards, F. Xu and C. L. Perrin, J. Am. Chem. Soc., 1995, 117, 3468 CrossRef CAS; J. F. Bartoli, P. Battioni, W. R. De Foor and D. Mansuy, J. Chem. Soc., Chem. Commun., 1994, 23 RSC.
  11. A. J. Allentoff, J. L. Bolton, A. Wilks, J. A. Thompson and P. R. Ortiz de Montellano, J. Am. Chem. Soc., 1992, 114, 9744 CrossRef CAS.
  12. D. Mansuy, P. Battioni and J.-P. Renaud, J. Chem. Soc., Chem. Commun., 1984, 1255 RSC.
  13. K. Yamaguchi, Y. Watanabe and I. Morishima, J. Am. Chem. Soc., 1993, 115, 4058 CrossRef CAS.