Catalytic Activities of CuSO4/Al2O3 in Dehydrogenation of Arenes by Dioxygen
- 1 May 1997
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 62 (10) , 3194-3199
- https://doi.org/10.1021/jo961377j
Abstract
The oxidation reactions of hydroquinones, 2-naphthols, or 2,6-di-tert-butylphenol efficiently occurred by catalysis with alumina-supported copper(II) sulfate to give the corresponding benzoquinones, 1,1‘-bi-2-naphthols, and 4,4‘-diphenoquinone, respectively, in good yields. The synthetic potentiality of the catalytic reactions was demonstrated by easy isolation of the final products using only filtration and solvent evaporation as well as by application to large-scale syntheses of the benzoquinones and binaphthols. The catalysis with alumina-supported copper(II) sulfate was also applied to the oxidative intramolecular coupling of 5,5‘-diacenaphthene to the corresponding perylene compound.Keywords
This publication has 31 references indexed in Scilit:
- A new catalytic system for aerobic oxidative coupling of 2-naphthol derivatives by the use of CuCl-amine complex: a practical synthesis of binaphthol derivativesTetrahedron Letters, 1994
- Oxidation of Phenols and Hydroquinones by Dioxygen Catalyzed by Mixed Addenda Heteropolyoxometalate on Active Carbon (NPV6Mo6/C)Chemistry Letters, 1994
- Dehydrosilylation versus α-coupling in the electron-transfer of enol silyl ethers to quinones. Strong solvent effect on photogenerated ion pairsJournal of the Chemical Society, Perkin Transactions 2, 1993
- Oxidation of phenols by molecular oxygen catalysed by transition metal complexes. Comparison between the activity of various cobalt and manganese complexes and the role of peroxy intermediatesJournal of the Chemical Society, Perkin Transactions 1, 1984
- Thallium in organic synthesis. 58. Regiospecific intermolecular oxidative dehydrodimerization of aromatic compounds to biaryls using thallium(III) trifluoroacetateJournal of the American Chemical Society, 1980
- Sodium chromate oxidation of enol benzoates. Allylic oxidation versus a novel rearrangementJournal of the Chemical Society, Perkin Transactions 1, 1977
- Thallium in organic synthesis. XLII. Direct oxidation of 4-substituted phenols to 4,4-disubstituted cyclohexa-2,5-dienones using thallium(III) nitrateThe Journal of Organic Chemistry, 1976
- 557. Preparation of p-benzoquinonesJournal of the Chemical Society, 1963
- Oxidation Processes. XII.1 The Autoxidation of Hydroquinone and of the Mono-, Di- and TrimethylhydroquinonesJournal of the American Chemical Society, 1938
- Über das 2.7.2′.7′‐Tetraoxydinaphthyl‐(1.1′)Berichte der deutschen chemischen Gesellschaft (A and B Series), 1937