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Effects of metal and porphyrin structure on the yield and chemoselectivity of naphthalene oxidation: a comparative study for manganese and iron

Hamid Reza Khavasi

Department of Chemistry, Shahid Beheshti University, Evin, Tehran 1983963113, Iran

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and

Nasser Safari

Department of Chemistry, Shahid Beheshti University, Evin, Tehran 1983963113, Iran

Corresponding author, fax: +98 21-2403041

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https://doi.org/10.1142/S1088424605000137Cited by:10 (Source: Crossref)

Abstract

Oxidation of naphthalene was performed with various manganese and iron porphyrins as catalysts and metachloroperbenzoic acid, tert-butylhydroperoxide, and hydrogenperoxide as oxidants, in the presence of imidazole as cocatalyst. With m-CPBA, in low concentration of catalyst, iron porphyrin shows a higher catalytic activity than manganese porphyrin, while a greater amount of manganese porphyrin is needed for having a good catalyst. In the presence of excess amount of H₂O₂ oxidant in CH₃OH solvent, manganese porphyrin acts better than iron porphyrin; however with the same oxidant and in aprotic solvent such as CH₃CN:CH₂Cl₂ again iron shows a higher activity than manganese. Moreover, the effects of metalloporphyrin concentration on the selectivity, activity and stability of catalyst were studied in H₂O₂-catalytic oxidation.

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References

R. A. Sheldon and J. K. Kochi , Metal-catalyzed oxidation of organic compounds ( Academic Press , New York , 1981 ) . Google Scholar
R. A. Sheldon , Applied homogeneous catalysis with organometallic compounds , eds. B. Cornils and W. A. Herrman ( VCH , Weinheim , 1996 ) . Google Scholar
P. Ortiz de Montellano , Cytochrome P-450: Structure, Mechanism and Biochemistry ( Plenum Press , New York , 1995 ) . Crossref, Google Scholar
a) Traylor TG and Miksztal AR. J. Am. Chem. Soc. 1997; 111: 7443. b) Traylor TG, Nakano T and Dunlap BE. J. Am. Chem. Soc. 1986; 108: 2782 . Google Scholar
J. T. Groves and T. E. Nemo, J. Am. Chem. Soc. 105, 5786 (1983), DOI: 10.1021/ja00356a015. Crossref, Web of Science, Google Scholar
S. Campestrini and U. Tonellato, J. Mol. Catal. A: Chem. 171, 37 (2001), DOI: 10.1016/S1381-1169(01)00098-X. Crossref, Web of Science, Google Scholar
I. D. Cunninghamet al., Tetrahedron 57, 6847 (2001), DOI: 10.1016/S0040-4020(01)00639-1. Crossref, Web of Science, Google Scholar
a) Haber J, Iwanejko R, Pottowicz J, Battioni P and Mansuy D. J. Mol. Catal. A: Chem. 2000; 152: 111. b) Haber J, Iwanejko R, Pottowicz J, Battioni P and Mansuy D. J. Mol. Catal. A: Chem. 2000; 152: 117 . Google Scholar
R. A. Sheldon , Metalloporphyrins in Catalytic Oxidations ( Marcel Dekker , New York , 1994 ) . Google Scholar
a) Rose E, Quelquejeu M, Pandian RP, Lecas-Nawrocka A, Vilar A, Ricart G, Collman JP, Wang Z and Straumanis A. Polyhedron. 2000: 19; 581. b) Rose E, Ren Q-Z and and Rioletti B. Chem–Eur. J. 2004; 10: 224 . Google Scholar
T. G. Trayloret al., J. Am. Chem. Soc. 114, 1308 (1992), DOI: 10.1021/ja00030a028. Crossref, Web of Science, Google Scholar
C.-C. Guoet al., J. Mol. Catal, A: Chem. 192, 289 (2003), DOI: 10.1016/S1381-1169(02)00449-1. Crossref, Web of Science, Google Scholar
C. Guoet al., J. Mol. Catal, A: Chem. 192, 295 (2000), DOI: 10.1016/S1381-1169(02)00421-1. Crossref, Web of Science, Google Scholar
J.-W. Huanget al., J. Mol. Catal, A: Chem. 156, 275 (2000), DOI: 10.1016/S1381-1169(99)00447-1. Crossref, Web of Science, Google Scholar
J. T. Groves and P. Viski, J. Org. Chem. 55, 3628 (1990), DOI: 10.1021/jo00298a046. Crossref, Web of Science, Google Scholar
a) Sorokin A and Meunier B. Eur. J. Inorg. Chem. 1998: 1269. b) Song R, Sorokin A, Bernadou J, and Meunier B. J. Org. Chem. 1997; 62: 673. c) Sorokin A, De Suzzomi-Dezard S, Poullain D, Noël JP and Meunier B, J. Am. Chem. Soc. 1996; 118: 7410. d) Hadasch A, Sorokin A, Rabion A and Meunier B. New. J. Chem. 1998: 45. e) Sorokin A, Seris JL and Meunier B. Science (Washington, DC, U. S.) 1995; 268: 1163. f) Meunier B and Sorokin A. Acc. Chem. Res. 1997; 30: 470 . Google Scholar
N. Safariet al., J. Porphyrins Phthalocyanines 4, 285 (2000). Link, Web of Science, Google Scholar
A. Goldet al., J. Mol. Catal. A: Chem. 125, 23 (1997), DOI: 10.1016/S1381-1169(97)00053-8. Crossref, Web of Science, Google Scholar
a) Bartoli JF, Mansuy VM, Ozette KL, Palacio M, Battioni P and Mansuy D. Chem. Commun. (Cambridge, U. K.) 2000: 827. b) Bartoli JF, Le Barch K, Palacio M, Battioni P and Mansuy D. Chem. Commun. (Cambridge, U.K.) 2001: 1718. c) Carrier MN, Scheer C, Gouvine P, Bartoli JF, Battioni P and Mansuy D. Tetrahedron. Lett. 1990; 31: 6645. d) Meunier B, Robert A, Pratviel G and Bernadou J. In The Porphyrin Handbook, Vol. 4, Kadish KM, Smith KM and Guilard R. (Eds.) Academic Press: New York, 2000; pp 119-187 . Google Scholar
J. P. Collman, P. D. Hamton and J. I. Brauman, J. Am. Chem Soc. 112, 2986 (1990), DOI: 10.1021/ja00164a022. Crossref, Web of Science, Google Scholar
P. S. Traylor, D. Dolphin and T. G. Traylor, J. Chem. Soc., Chem. Commun. 279 (1984), DOI: 10.1039/c39840000279. Google Scholar
I. Artenau, N. Gregoire and D. Mansuy, New. J. Chem. 13, 581 (1989). Web of Science, Google Scholar
J. I. Stesune and D. Dolphin, Can. J. Chem. 65, 459 (1987). Crossref, Web of Science, Google Scholar
J. A. Smegal, B. C. Schardt and C. L. Hill, J. Am. Chem. Soc. 105, 3510 (1983), DOI: 10.1021/ja00349a024. Crossref, Web of Science, Google Scholar
H. R. Khavasi, S. S. H. Davarani and N. Safari, J. Mol. Catal. A: Chem. 188, 115 (2002), DOI: 10.1016/S1381-1169(02)00354-0. Crossref, Web of Science, Google Scholar
J. S. Lindsey, H. C. Hsu and I. C. Schreiman, Tetrahedron. Lett. 27, 4969 (1986), DOI: 10.1016/S0040-4039(00)85109-6. Crossref, Web of Science, Google Scholar
A. D. Adleret al., J. Inorg. Nucl. Chem. 32, 2443 (1970), DOI: 10.1016/0022-1902(70)80535-8. Crossref, Web of Science, Google Scholar
J. T. Groves and Z. Gross , Bioinorganic Chemistry , ed. D. P. Kessissoglou ( Kluwer Academic Publisher , The Netherlands , 1995 ) . Google Scholar
W. Namet al., J. Am. Chem. Soc. 122, 6641 (2000), DOI: 10.1021/ja000289k. Crossref, Web of Science, Google Scholar