A combined use of (NH4)2S2O8 as the terminal oxidant and AgNO3 as the catalyst can effect the oxidation of aromatic alcohols and diols in hexane in the presence of montmorillonite K10 preloaded with a small amount of water, giving the corresponding carbonyl compounds in high yields under relatively mild conditions.
Part of the results has been reported previously; HiranoM., YakabeS., and MorimotoT., 4th International Symposium on Supported Reagents and Catalysts in Chemistry, St. Andrews, Scotland, 2000, Abstracts P-1.
2.
MijsW.J., and de JongeC. R. H. I. (ed.), Organic Syntheses by Oxidation with Metal Compounds, Plenum Press, New York, 1986; A. H. Haines, Methods for the Oxidation of Organic Compounds. Alcohols, Alcohol Derivatives, Alkyl Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds, Hydroxyarenes, and Aminoarenes, Academic Press, London, 1988, chap. 2; M. Hudlicky, Oxidations in Organic Chemistry, Am. Chem. Soc., Washington, DC, 1990, pp. 114–163.
3.
ClarkJ.H., and MacquarrieD. J., Chem. Soc. Rev., 1996, 303.
4.
Comprehensive review books are available: (a) ClarkJ. H., and RhodesC. N., Clean Synthesis Using Porous Inorganic Solid Catalysts and Supported Reagents, RSC, Cambridge, 2000; (b) B.K. Hodnett, A.P. Kybett, J.H. Clark and K. Smith (eds), Supported Reagents and Catalysts in Chemistry, RSC, Cambridge, 1998; (c) J.H. Clark, Catalysis of Organic Reactions by Supported Inorganic Reagents, VCH, New York, 1994; (d) J.H. Clark, A.P. Kybett and D.J. Macquarrie, Supported Reagents. Preparation, Analysis, and Applications, VCH, New York, 1992; (e) M. Balogh and P. Laszlo, Organic Chemistry Using Clays, Springer-Verlag, Berlin, 1993; (f) K. Smith (ed.), Solid Supports and Catalyst in Organic Synthesis, Ellis Horwood, Chichester, 1992; (g) P. Laszlo (ed.), Preparative Chemistry Using Supported Reagents, Academic Press, San Diego, 1987.
5.
(a) HiranoM., YakabeS., ClarkJ. H., and MorimotoT., J. Chem. Soc., Perkin Trans. 1, 1996, 2693; (b) M. Hirano, S. Yakabe, H. Monobe, J.H. Clark and T. Morimoto, J. Chem. Soc., Perkin Trans. 1, 1997, 3081; (c) S. Yakabe, M. Hirano and T. Morimoto, Can. J. Chem., 1998, 76, 1916.
6.
(a) HiranoM., KomiyaK., and MorimotoT., Org. Prep. Proced. Int., 1995, 27, 703; (b) M. Hirano, H. Kuroda and T. Morimoto, Bull. Chem. Soc. Jpn., 1990, 63, 2433; (c) M. Hirano and T. Morimoto, Bull. Chem. Soc. Jpn., 1989, 62, 4069; (d) M. Hirano, T. Morimoto and K. Itoh, Bull. Chem. Soc. Jpn., 1988, 61, 3749.
7.
MinisciF., CitterioA., and GiordanoC., Acc. Chem. Res., 1983, 16, 27; D. A. House, Chem. Rev., 1962, 62, 185.
8.
BehrmanE.J., Org. React., 1988, 35, pp. 421; L.F. Fieser, Org. React., 1942, 1, pp. 129.
9.
(a) BaconR.G. R., and DoggartJ. R., J. Chem. Soc., 1960, 1332; (b) F.P. Greenspan and H.M. Woodburn, J. Am. Chem. Soc., 1954, 76, 6345; (c) T. Caronna, A. Citterio, L. Grossi, F. Minisci and K. Ogawa, Tetrahedron, 1976, 32, 2741; (d) J.E. McIsaac, Jr. and J.O. Edwards, J. Org. Chem., 1969, 34, 2565; (e) L. Dogliotti and E. Hayon, J. Phys. Chem., 1967, 71, 2511.
10.
Ref. 5(b) and references cited therein.
11.
For example, see: BelliA., GiordanoC., and CitterioA., Synthesis, 1980, 477.
12.
BuckinghamJ., and MacdonaldF. (eds), Dictionary of Organic Compounds, Chapman & Hall, London, 6th edn., 1996, pp. 637.
13.
PouchertC.J. (ed.), The Aldrich Library of NMR Spectra, Aldrich Chemical Co., Milwaukee, 2nd edn, vol. 2, 1983.
14.
The Library of FT-IR SpectraSigma-Aldrich Co., Milwaukee, 2nd edn, vol. 2, 1997.
