A reagent combination of (NH4)2S2O8, a catalytic amount of AgNO3, in general, or Cu(NO3)2 in particular, and moist montmorillonite K10 clay in hexane regenerates the parent carbonyl compounds in high yields under relatively mild conditions.
Preceding paper; HiranoM., KojimaK., YakabeS., and MorimotoT., J. Chem. Res. (S), in press.
2.
GreeneT.W., and WutsP. G. M., Protective Groups in Organic Synthesis, John Wiley & Sons, New York, 2nd. ed., 1991; M.B. Smith, Organic Synthesis, McGraw-Hill, New York, 1994, chap. 7; P.J. Kocienski, Protecting Groups, Thieme Verlag, Stuttgart, 1994; J.R. Hanson, Protectiing Groups in Organic Synthesis, Sheffield Academic Press, 1999, Sheffield.
3.
For example, see; AdamsJ. P., J. Chem. Soc., Perkin Trans. 1, 2000, 125.
4.
Comprehensive review books of supported reagents and catalysts are available: (a) ClarkJ.H., and RhodesC. N., Clean Synthesis Using Porous Inorganic Solid Catalysts and Supported Reagents, RSC, Cambridge, 2000; (b) Supported Reagents and Catalysts in Chemistry, ed. HodnettB.K., KybettA. P., ClarkJ. H., and SmithK., 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) Solid Supports and Catalyst in Organic Synthesis, ed. K. Smith, Ellis Horwood, Chichester, 1992; (g) Preparative Chemistry Using Supported Reagents, ed. P. Laszlo, Academic Press, San Diego, 1987.
5.
(a) VarmaR.S., DahiyaR., and SainiR. K., Tetrahedron Lett., 1997, 38, 8819; (b) R. S. Varma and H.M. Meshram, Tetrahedron Lett., 1997, 38, 5427; (c) R. S. Varma and H.M. Meshram, Tetrahedron Lett., 1997, 38, 7973; (d) R.S. Varma and R.K. Saini, Tetrahedron Lett., 1997, 38, 2623; (e) R.S. Varma, M. Varma and A.K. Chatterjee, J. Chem. Soc., Perkin Trans. 1, 1993, 999 and R.S. Varma, A.K. Chatterjee and M. Varma, Tetrahedron Lett., 1993, 34, 4603 and 3207; (f) R.S. Varma, J.B. Lamture and M. Varma, Tetrahedron Lett., 1993, 34, 3029.
6.
For oxidations with peroxodisulfates, see reviews: MinisciF., CitterioA., and GiordanoC., Acc. Chem. Res., 1983, 16, 27; D.A. House, Chem. Rev., 1962, 62, 185; E.J. Behrman, Org. React., 1988, 35, pp. 421; L. F. Fieser, Org. React., 1942, 1, pp. 129.
7.
HiranoM., YakabeS., ClarkJ. H., and MorimotoT., J. Chem. Soc., Perkin Trans. 1, 1996, 2693; M. Hirano, S. Yakabe, H. Monobe, J.H. Clark and T. Morimoto, J. Chem. Soc., Perkin Trans. 1, 1997, 3081; S. Yakabe, M. Hirano and T. Morimoto, Can. J. Chem., 1998, 76, 1916.
8.
BrooksS.G., EvansR. M., GreenG. F. H., HuntJ. S., LongA. G., MooneyB., and WymanL. J., J. Chem. Soc., 1958, 4614.
9.
ClarkJ. H., and MacquarrieD. J., Chem. Soc. Rev., 1996, 303.
10.
HiranoM., YakabeS., and MorimotoT., unpublished data.
11.
Dictionary of Organic Compounds, ed. BuckinghamJ., and MacdonaldF., Chapman & Hall, London, 6th edn., 1996, pp. 637.
12.
The Aldrich Library of NMR Spectra, ed. PouchertC.J., Aldrich Chemical Co., Milwaukee, 2nd edn, vol. 2, 1983.
13.
The Library of FT-IR Spectra, Sigma-Aldrich Co., Milwaukee, 2nd edn, vol. 2, 1997.
