%0 Journal Article %1 ISI:000177937800014 %A Khavasi, HR %A Davarani, SSH %A Safari, N %C PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS %D 2002 %I ELSEVIER SCIENCE BV %J JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL %K P-450; acid aromatic hydrocarbon; iron-porphyrin; metachloroperbenzoic naphthalene} oxidation; polycyclic {cytochrome %N 1-2 %P 115-122 %R 10.1016/S1381-1169(02)00354-0 %T Remarkable solvent effect on the yield and specificity of oxidation of naphthalene catalyzed by iron (III)porphyrins %V 188 %X Oxidation of naphthalene was performed with tetrakis(pentaflourophenyl)porphyrin iron(III)chloride ((F20TPPFeCl)-Cl-III), or tetrakis(2,6-dichlorophenyl)porphyrin iron(III)chloride ((TDCPPFeCl)-Cl-III), or tetramesitylporphyrin iron(III)chloride ((TMPFeCl)-Cl-III) as catalyst and metachloroperbenzoic acid or pentafluoroiodosylbenzene or tert-burythydroperoxide as oxidant in different media in the presence of imidazole as cocatalyst. In aprotic solvent (CH3CN:CH2Cl2, 1:1) and in the presence of (F20TPPFeCl)-Cl-III, 1-naphthol, 2-naphthol and 1,4-naphthoquinone yields based on metachloroperbenzoic acid oxidant were 77.7, 2.1 and 5.6\%, respectively. The best yield for 1,4-naphthoquinone in methanol with (F20TPPFeCl)-Cl-III was 52.8\%. The effect of bases on the yield and specificity of the naphthalene oxidation were studied. When imidazole changed to pyridine in (F20TPPFeCl)-Cl-III, the yield of 1-naphthol decreased from 77.7 to 55.3\%, whereas for (TDCPPFeCl)-Cl-III catalyst, the yield changed from 61.1 to 18.3\%. (C) 2002 Elsevier Science BV All rights reserved.

@article{ISI:000177937800014, abstract = {{Oxidation of naphthalene was performed with tetrakis(pentaflourophenyl)porphyrin iron(III)chloride ((F20TPPFeCl)-Cl-III), or tetrakis(2,6-dichlorophenyl)porphyrin iron(III)chloride ((TDCPPFeCl)-Cl-III), or tetramesitylporphyrin iron(III)chloride ((TMPFeCl)-Cl-III) as catalyst and metachloroperbenzoic acid or pentafluoroiodosylbenzene or tert-burythydroperoxide as oxidant in different media in the presence of imidazole as cocatalyst. In aprotic solvent (CH3CN:CH2Cl2, 1:1) and in the presence of (F20TPPFeCl)-Cl-III, 1-naphthol, 2-naphthol and 1,4-naphthoquinone yields based on metachloroperbenzoic acid oxidant were 77.7, 2.1 and 5.6\%, respectively. The best yield for 1,4-naphthoquinone in methanol with (F20TPPFeCl)-Cl-III was 52.8\%. The effect of bases on the yield and specificity of the naphthalene oxidation were studied. When imidazole changed to pyridine in (F20TPPFeCl)-Cl-III, the yield of 1-naphthol decreased from 77.7 to 55.3\%, whereas for (TDCPPFeCl)-Cl-III catalyst, the yield changed from 61.1 to 18.3\%. (C) 2002 Elsevier Science BV All rights reserved.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS}}, affiliation = {{Safari, N (Reprint Author), Shahid Beheshti Univ, Dept Chem, Tehran 19839, Iran. Shahid Beheshti Univ, Dept Chem, Tehran 19839, Iran.}}, article-number = {{PII S1381-1169(02)00354-0}}, author = {Khavasi, HR and Davarani, SSH and Safari, N}, author-email = {{n-safari@cc.sbu.ac.ir}}, biburl = {https://www.bibsonomy.org/bibtex/24b4c4836613b4f48f53899fa0b787230/hkhavasi}, cited-references = {{ADLER AD, 1970, J INORG NUCL CHEM, V32, P2443, DOI 10.1016/0022-1902(70)80535-8. ALMARSSON O, 1995, J AM CHEM SOC, V117, P4533, DOI 10.1021/ja00121a012. Barkanova SV, 1996, TETRAHEDRON LETT, V37, P1637, DOI 10.1016/0040-4039(96)00079-2. Bartoli JF, 2000, CHEM COMMUN, P827, DOI 10.1039/b001776k. CARRIER MN, 1990, TETRAHEDRON LETT, V31, P6645, DOI 10.1016/S0040-4039(00)97136-3. Collman JP, 1998, J AM CHEM SOC, V120, P425, DOI 10.1021/ja973111f. Ortiz de Montellano P. R., 1995, CYTOCHROME P 450 STR. Dolphin D, 1997, ACCOUNTS CHEM RES, V30, P251, DOI 10.1021/ar960126u. Gold A, 1997, J MOL CATAL A-CHEM, V125, P23, DOI 10.1016/S1381-1169(97)00053-8. GONSALVES AMD, 1994, J CHEM SOC P1, V15, P2053. GROVES JT, 1983, J AM CHEM SOC, V105, P5786, DOI 10.1021/ja00356a015. GUROFF G, 1967, SCIENCE, V157, P1524, DOI 10.1126/science.157.3796.1524. HAMMEL KE, 1992, MET IONS BIOL SYST, V28, P41. Jin N, 1999, J AM CHEM SOC, V121, P2923, DOI 10.1021/ja984429q. LIPSCOMB JD, 1992, MET IONS BIOL SYST, V28, P243. MANSUY D, 1993, COORDIN CHEM REV, V125, P129, DOI 10.1016/0010-8545(93)85013-T. MEUNIER B, 1992, CHEM REV, V92, P1411, DOI 10.1021/cr00014a008. Nam W, 2000, J AM CHEM SOC, V122, P10805, DOI 10.1021/ja0010554. Nam WO, 2000, J AM CHEM SOC, V122, P6641, DOI 10.1021/ja000289k. Safari N, 2001, J MOL CATAL A-CHEM, V171, P115, DOI 10.1016/S1381-1169(01)00077-2. Safari N, 2000, J PORPHYR PHTHALOCYA, V4, P285, DOI 10.1002/(SICI)1099-1409(200004/05)4:3<285::AID-JPP215>3.3.CO;2-I. SCHEMEISSER M, 1967, CHEM BER, V100, P1633. Sheldon R. A., 1994, METALLOPORPHYRINS CA. Song R, 1997, J ORG CHEM, V62, P673, DOI 10.1021/jo961421v. SOROKIN A, 1995, SCIENCE, V268, P1163, DOI 10.1126/science.268.5214.1163. Sorokin A., 1998, EUR J INORG CHEM, V9, P1269. Sorokin AB, 2000, CATAL TODAY, V57, P45, DOI 10.1016/S0920-5861(99)00312-0. TRAYLOR TG, 1989, J AM CHEM SOC, V111, P7443, DOI 10.1021/ja00201a026. TRAYLOR TG, 1990, J AM CHEM SOC, V112, P178, DOI 10.1021/ja00157a029. TRAYLOR TG, 1985, J AM CHEM SOC, V107, P5537, DOI 10.1021/ja00305a042. WATANABE Y, 1991, INORG CHEM, V30, P2581, DOI 10.1021/ic00012a002. Yan Y, 2000, J MOL CATAL A-CHEM, V157, P65, DOI 10.1016/S1381-1169(99)00440-9.}}, doc-delivery-number = {{592KX}}, doi = {{10.1016/S1381-1169(02)00354-0}}, interhash = {4dc0ccdf19558011e554d0cf3cca05d2}, intrahash = {4b4c4836613b4f48f53899fa0b787230}, issn = {{1381-1169}}, journal = {{JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL}}, journal-iso = {{J. Mol. Catal. A-Chem.}}, keywords = {P-450; acid aromatic hydrocarbon; iron-porphyrin; metachloroperbenzoic naphthalene} oxidation; polycyclic {cytochrome}, keywords-plus = {{HYDROGEN-PEROXIDE; EPOXIDATION REACTIONS; IRON(III) PORPHYRINS; SELECTIVE OXIDATION; AROMATIC-COMPOUNDS; AQUEOUS-SOLUTION; HYDROXYLATION; COMPLEX; METALLOPORPHYRINS; HYDROPEROXIDES}}, language = {{English}}, month = {{SEP 30}}, number = {{1-2}}, number-of-cited-references = {{32}}, pages = {{115-122}}, publisher = {{ELSEVIER SCIENCE BV}}, research-areas = {{Chemistry}}, times-cited = {{38}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Remarkable solvent effect on the yield and specificity of oxidation of naphthalene catalyzed by iron (III)porphyrins}}, type = {{Article}}, unique-id = {{ISI:000177937800014}}, usage-count-last-180-days = {{0}}, usage-count-since-2013 = {{19}}, volume = {{188}}, web-of-science-categories = {{Chemistry, Physical}}, year = {{2002}} }