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DOI: 10.1039/A702069D (Paper) Reference Section for: J. Chem. Res. (S), 1997, 462-463

Zeolite H-ZSM 5 Catalysed Oxidation of Alcohols with Chromium Trioxide. Part 9.1 General Synthetic Methods†

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Sangeeta V. Pitre, M. Venkat Ram Reddy and Yashwant D. Vankar

Abstract

A variety of alcohols are oxidised to the corresponding carbonyl compounds in excellent yields by chromium trioxide–H-ZSM 5 in dichloromethane at room temperature.

References

  1. Part 8, R. Kumareswaran and Y. D. Vankar, Synth. Commun., submitted for publication Search PubMed.
  2. B. M. Trost and I. Fleming, Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, pp. 251–327 Search PubMed.
  3. R. C. Larock, Comprehensive Organic Transformations, VCH, New York, 1989, p. 604 Search PubMed.
  4. A. Mancuso, S.-L. Huang and D. Swern, J. Org. Chem., 1978, 43, 2480 Search PubMed; M. Hirano, H. Kuroda and T. Morimoto, Bull. Chem. Soc. Jpn., 1990, 63, 2433 Search PubMed; W.-X. Lou and J.-D. Lou, Synth. Commun., 1992, 767 Search PubMed; S. Aït-Mohand, F. Hénin and J. Muzart, Tetrahedron Lett., 1995, 36, 2473 Search PubMed; A. P. de Oliveira Filho, B. G. Moreira, P. J. S. Moran and J. A. R. Rodrigues, Tetrahedron Lett., 1996, 37, 5029 Search PubMed.
  5. D. B. Dess and J. C. Martin, J. Org. Chem., 1983, 48, 4155 Search PubMed.
  6. (a) A. Bowers, T. G. Halsall, E. R. H. Jones and A. J. Lemin, J. Chem. Soc., 1953, 2548 Search PubMed; (b) J. C. Collins and W. W. Hess, Org. Synth., 1972, 52, 5 Search PubMed; (c) E. J. Corey and J. W. Suggs, Tetrahedron Lett., 1975, 2647 Search PubMed; (d) E. J. Corey and G. Schmidt, Tetrahedron Lett., 1979, 399 Search PubMed.
  7. D. Basavaiah, P. Dharma Rao and R. S. Hyma, Tetrahedron, 1996, 52, 8001 Search PubMed and references cited therein.
  8. The Bayliss–Hillman product used was EtO2CC([double bond, length as m-dash]CH)C(OH)Ph.
  9. Y. Tamaru, Y. Yamamoto, Y. Yamada and Z.-I. Yoshida, Tetrahedron Lett., 1979, 1401 Search PubMed.
  10. Y. D. Vankar, M. V. Ram Reddy and N. C. Chaudhuri, Tetrahedron, 1994, 50, 11 057 Search PubMed.
  11. N. Tanaka, H. Suemune and K. Sakai, Tetrahedron: Asymmetry, 1992, 3, 1075 Search PubMed.
  12. A. Gupta, A. Haque and Y. D. Vankar, Chem. Commun., 1996, 1653 Search PubMed.
  13. Under these conditions oxidation of geraniol in 1,2-dichloroethane, in carbon tetrachloride and in chloroform, required 9, 10 and 9 h to give geranial in 76, 85 and 82% yields respectively.
  14. W. Holderich, M. Hesse and F. Naumann, Angew. Chem., Int. Ed. Engl., 1988, 226 Search PubMed; M. E. Davis, Acc. Chem. Res., 1993, 26, 111 Search PubMed.
  15. E. Santaniello, F. Ponti and A. Manzocchi, Synthesis, 1978, 534 Search PubMed.
  16. S. J. Flatt, G. W. J. Fleet and B. J. Taylor, Synthesis, 1979, 815 Search PubMed.
  17. M. V. Ram Reddy, S. V. Pitre, I. Bhattacharya and Y. D. Vankar, Synlett, 1996, 241 Search PubMed and references cited therein.
  18. H-ZSM 5 Zeolite (MFI) was prepared by calcination of NH4-ZSM 5 (obtained from PQ Zeolites B. V., The Netherlands) at 500 °C for 8 h. Si∶Al = 35 and the pore diameters are 5.1 × 5.5 Å and 5.4 × 5.6 Å.
  19. Y. Tamaru, T. Ko, H. Kondo and H. Annoura, Tetrahedron Lett., 1986, 27, 2117 Search PubMed.
  20. A. I. Vogel, A Text Book of Practical Organic Chemistry, Longman, London, 5th edn., 1989, p. 624 Search PubMed.
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