Hostname: page-component-586b7cd67f-2plfb Total loading time: 0 Render date: 2024-12-01T04:05:22.188Z Has data issue: false hasContentIssue false

Some organic syntheses with clay-supported reagents

Published online by Cambridge University Press:  09 July 2018

A. Cornelis
Affiliation:
Université de Liège, Institut de Chimie Organique B6, Sart-Tilman, B-4000 Liège, Belgium
P. Laszlo
Affiliation:
Université de Liège, Institut de Chimie Organique B6, Sart-Tilman, B-4000 Liège, Belgium
P. Pennetreau
Affiliation:
Université de Liège, Institut de Chimie Organique B6, Sart-Tilman, B-4000 Liège, Belgium

Abstract

Some uses of clay-supported reagents in fine organic synthesis are discussed, in particular the catalysis of the phase-transfer preparation of formaldehyde acetals by quaternary ammonium montmorillonites. The preparation and some applications of clay-supported ferric nitrate, a new reagent which oxidizes alcohols into carbonyl derivatives, couples thiols into disulphides, nitrates phenols, and oxidatively couples pyrrole and benzaldehyde into tetra-phenylporphyrin, are also described

Type
Research Article
Copyright
Copyright © The Mineralogical Society of Great Britain and Ireland 1983

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Adler, A.D., Skar, L., Longo, F.R., Finarelli, J.D. & Finarelli, M.C. (1968) A mechanistic study of the synthesis of meso-tetraphenylporphyrin (1). J. Heterocycl. Chem. 5, 669678.Google Scholar
Aldred, S.E., Williams, D.L.H. & Garley, M. (1982) Kinetic and mechanism of the nitrosation of alcohols, carbohydrates and a thiol. J. C. S. Perkin Trans. 2 777782.CrossRefGoogle Scholar
Audley, C.J., Baulch, D.L. & Campbell, I.M. (1982) A new method for the synthesis of nitroethane, ethyl nitrite, and ethyl nitrate. J. C. S. Chem. Comm. 10531055.Google Scholar
Barret, J., Debenham, D.F. & Glauser, J. (1965) The electronic spectrum and photolysis of S nitrosotoluène α thiol. J. C. S. Chem. Comm. 248249.Google Scholar
Barton, D.H.R. & Beaton, J.M. (1961) A synthesis of aldosterone acetate. J. Am. Chem. Soc. 83, 40834089.Google Scholar
Barton, D.H.R., Ramsay, G.C. & Wege, D.W. (1967) Photochemical transformations, part XXI. A comparison of the photolysis and pyrolysis of organic nitrites. J. Chem. Soc. C 19151919.CrossRefGoogle Scholar
Bergaya, F. & van Damme, H. (1982) Stability of metalloporphyrines adsorbed on clays: a comparative study. Geochim. Cosmochim. Acta 46, 349360.Google Scholar
Bouquant, J., Delville, A., Grandjean, J. & Laszlo, P. (1982) Na+ complexes with spiro-bis-crown ethers: stoichiometries, stabilities and labilities in pyridine solution. J. Am. Chem. Soc. 104, 686691.Google Scholar
Cady, S.S. & Pinnavaia, T.J. (1977) Porphyrine intercalation in mica type silicate. Inorg. Chem. 17, 15011507.CrossRefGoogle Scholar
Capozzi, G. & Modena, G. (1974) Oxidation of thiols. Pp. 801803 in: The Chemistry of the Thiol Group (Patai, S., editor) Wiley, New York.Google Scholar
Chalais, S., Delville, A., Detellier, C., Gerstmans, A. & Laszlo, P. (1983) Chelation of Na+ cations in non-aqueous solvents. Structural requirements and methodological considerations. J. Sol. Chem. 12, 3340.Google Scholar
Cornelis, A., Depaye, N., Gerstmans, A. & Laszlo, P. (1983) Clay-supported reagent. IV. A novel coupling of thiols into disulfide via thionitrite intermediates, using a clay-supported nitrosation reagent. Tetrahedron Lett. 24, 31033106.Google Scholar
Cornelis, A., Herze, P.Y. & Laszlo, P. (1982) Clay-supported reagent. III. The intermediacy of nitrous esters in the oxydation of alcohols by clay-supported ferric nitrate. Tetrahedron Lett. 23, 50355038.Google Scholar
Cornelis, A. & Laszlo, P. (1980) Oxidations of alcohols by clay-supported iron(III) nitrate. A new efficient oxidizing agent. Synthesis 849850.Google Scholar
Cornelis, A. & Laszlo, P. (1982) Clay-supported reagents. II. Quaternary ammonium exchanged montmorillonite as catalysts in the phase-transfer preparation of symmetrical formaldehyde acetals. Synthesis 162163.Google Scholar
Cornelis, A., Laszlo, P. & Cambillau, C. (1978) Structure en solution de l'acétylacétate d'éthyle sodique en presence d'éthers-couronnes: étude par RMN du sodium-23. J. Chem. Res. (S) 462-463; (M) 54575476.Google Scholar
Caubere, P. (1982) Le Transfert de Phase et son Utilisation en Chimie Organique. Masson, Paris.Google Scholar
Dehmlow, E.V. & Dehmlow, S.S. (1980) Phase-Transfer Catalysis. Monographs in Modern Chemistry. 11. Verlag Chemie, Weinheim.Google Scholar
Dehmlow, E.V. & Schmidt, J. (1976) Anwendungen der Phasen-Transfer Katalyse 2: Diaryloxymethane und Formaldehydeacetale. Tetrahedron Lett. 9596.CrossRefGoogle Scholar
Fetizon, M. & Golfier, M. (1968) Oxidation selective des alcools par le carbonate d'argent. C.R. Acad. Sci. serie C 267, 900903.Google Scholar
Frechet, J.M.J. (1981) Synthesis and applications of organic polymers as support and protecting groups. Tetrahedron 37, 663683.Google Scholar
McKillop, A. & Young, D.W. (1979) Organic synthesis using supported reagents. Synthesis 401-422; 481500.Google Scholar
Merrifield, R.B. (1963) Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 85, 21492154.Google Scholar
Monzef-Mirzai, P. & McWhinnie, W.R. (1981) Clay-supported catalysts: an extension of phase transfer catalysis. Inorg. Chim. Acta 52, 211214.Google Scholar
Oae, S., Fukushima, D. & Kim, Y.H. (1977) Novel method of activating thiols by their conversion into thionitrites with dinitrogen tetroxide. J. C. S. Chem. Comm. 407408.Google Scholar
Ouertani, M., Girard, P. & Kagan, H.B. (1982) Selective nitration of phenols catalysed by lanthanum III nitrate. Tetrahedron Lett. 23, 43154318.CrossRefGoogle Scholar
Posner, G.H. (1978) Organic reactions at alumina surfaces. Angew. Chem. Int. Ed. Engl. 17, 487496.Google Scholar
Riebsomer, J.L. (1945) The reactions of nitrogen tetroxide with organic compounds. Chem. Rev. 36, 157233.Google Scholar
Ross, D.S., Hum, G.P., Blucher, W.G. (1980) Catalysis of aromatic nitration by the lower oxides of nitrogen. J. C. S. Chem. Comm. 532533.Google Scholar
Seifert, W.K. (1963) Synthesis of nitro-olefins from olefin dinitrogen tetroxide adducts. J. Org. Chem. 28, 125129.CrossRefGoogle Scholar
Starks, C.M. & Liotta, C. (1978) Phase Transfer Catalysis. Principles and Techniques. Academic Press, New York.Google Scholar
van Zwet, H. & Kooyman, E.C. (1968) Sulfur compounds in free radical reactions. Part III. Thermal decomposition of triphenylmethylthionitrite. Recueil 87, 4548.Google Scholar
Weber, W.P. & Gokel, G.W. (1977) Phase Transfer Catalysis in Organic Synthesis. Reactivity and Structure Concepts in Organic Chemistry, 4. Springer Verlag, Berlin.Google Scholar