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.
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