Remarkable solvent effect on the yield and specificity of oxidation of naphthalene catalyzed by iron(III)porphyrins

✍ Scribed by Hamid Reza Khavasi; S.Saeed Hosseiny Davarani; Nasser Safari

• Publisher: Elsevier Science
• Year: 2002
• Tongue: English
• Weight: 96 KB
• Volume: 188
• Category: Article
• ISSN: 1381-1169
• DOI: 10.1016/s1381-1169(02)00354-0

✦ Synopsis

Oxidation of naphthalene was performed with tetrakis(pentaflourophenyl)porphyrin iron(III)chloride (F 20 TPPFe III Cl), or tetrakis(2,6-dichlorophenyl)porphyrin iron(III)chloride (TDCPPFe III Cl), or tetramesitylporphyrin iron(III)chloride (TMPFe III Cl) as catalyst and metachloroperbenzoic acid or pentafluoroiodosylbenzene or tert-butylhydroperoxide as oxidant in different media in the presence of imidazole as cocatalyst. In aprotic solvent (CH 3 CN:CH 2 Cl 2 , 1:1) and in the presence of F 20 TPPFe III Cl, 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 F 20 TPPFe III Cl was 52.8%. The effect of bases on the yield and specificity of the naphthalene oxidation were studied. When imidazole changed to pyridine in F 20 TPPFe III Cl, the yield of 1-naphthol decreased from 77.7 to 55.3%, whereas for TDCPPFe III Cl catalyst, the yield changed from 61.1 to 18.3%.