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Part of the book series: Homogeneous Catalysis in Organic and Inorganic Chemistry ((CMCO,volume 1))

Abstract

It was noted in Chapter I that in hydrogenation the process of addition of a metal hydride across an alkene bond is fundamentally reversible, i.e.:

Thus the mechanism of hydrogenation contains the possibility of alkene isomerisation since it is also evident that the reverse process of elimination of L n MH from the metal alkyl (2) may involve either hydrogen H(a), leading back to the parent alkene (1), or H(b) yielding an isomerised alkene.

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References

  1. J. A. Osborn, F. H. Jardine, J. F. Young, and G. Wilkinson: J. Chem. Soc. (A), 1711 (1966).

    Google Scholar 

  2. F. H. Jardine, J. A. Osborn, and G. Wilkinson: J. Chem. Soc. (A), 1574 (1967).

    Google Scholar 

  3. A. J. Birch and K. A. M. Walker: J. Chem. Soc. (C), 1894 (1966).

    Google Scholar 

  4. G. C. Bond and R. A. Hillyard: Disc. Faraday Soc. 46, 20 (1968).

    Article  Google Scholar 

  5. R. L. Augustine and J. van Peppen: Ann. New York Acad. Sci. 158, 482 (1969).

    Article  CAS  Google Scholar 

  6. R. L. Augustine and J. van Peppen: J. Chem. Soc. Chem. Comm., 495 (1970).

    Google Scholar 

  7. R. L. Augustine and J. van Peppen: J. Chem. Soc. Chem. Comm., 497 (1970).

    Google Scholar 

  8. B. Hudson, P. C. Taylor, D. E. Webster, and P. B. Wells: Discuss. Faraday Soc. 46, 37 (1968).

    Article  Google Scholar 

  9. D. F. Ewing, B. Hudson, D. E. Webster, and P. B. Wells: J. Chem. Soc. Dalton Trans., 1287 (1972).

    Google Scholar 

  10. J. E. Lyons: J. Chem. Soc. Chem. Comm., 562(1971).

    Google Scholar 

  11. J. E. Lyons : Org. Chem. 36, 2497 (1971).

    Article  CAS  Google Scholar 

  12. P. S. Hallman, B. R. McGarvey, and G. Wilkinson: Chem. Soc. (A), 3143(1968).

    Google Scholar 

  13. D. Rose, J. D. Gilbert, R. P. Richardson, and G. Wilkinson: Chem. Soc. (A), 2610 (1969).

    Google Scholar 

  14. J. G. Atkinson and M. O. Luke: Canadian J. Chem. 48, 3580 (1970).

    Article  CAS  Google Scholar 

  15. A. L. Odell, J. B. Richardson, and W. R. Roper: J. Catal. 8, 393 (1967).

    Article  CAS  Google Scholar 

  16. J. F. Biellman and M. J. Jung: J. Amer. Chem. Soc. 90, 1673 (1968).

    Article  Google Scholar 

  17. D. Evans, J. A. Osborn, and G. Wilkinson: J. Chem. Soc. (A), 3133 (1968).

    Google Scholar 

  18. M. Yagupsky and G. Wilkinson: J. Chem. Soc. (A), 941 (1970).

    Google Scholar 

  19. H. van Gaal, H. G. A. M. Cuppers, and A. van der Ent: J. Chem. Soc. Chem. Comm., 1694(1970).

    Google Scholar 

  20. P. Abley and F. J. McQuillin: J. Catal. 24, 536 (1972).

    Article  CAS  Google Scholar 

  21. A. G. Hinze and D. J. Frost: J. Catal. 24, 540 (1972).

    Article  Google Scholar 

  22. D. E. Minnikin, P. Abley, F. J. McQuillin, K. Kusamran, K. Maskens, and N. Polgar: Lipids 9, 135 (1974).

    Article  CAS  Google Scholar 

  23. P. Abley and F. J. McQuillin: Discuss. Faraday Soc. 46, 31 (1968).

    Article  Google Scholar 

  24. J. C. Bailar and H. Itatani: J. Amer. Chem. Soc. 89, 1592 (1967).

    Article  CAS  Google Scholar 

  25. H. Itatani and J. C. Bailar: J. Amer. Chem. Soc. 89, 1600 (1967).

    Article  CAS  Google Scholar 

  26. E. A. Emken, E. N. Frankel, and R. O. Butterfield: J. Amer. Oil Chem. Soc. 43, 14 (1966).

    Article  CAS  Google Scholar 

  27. E. N. Frankel, E. A. Emken, H. M. Peters, V. L. Davison, and R. O. Butterfield: J. Org. Chem. 29, 3292 (1964).

    Article  CAS  Google Scholar 

  28. E. N. Frankel, E. A. Emken, and Y. L. Davison: J. Amer. Oil Chem. Soc. 43, 307 (1966).

    Article  CAS  Google Scholar 

  29. E. N. Frankel and S. Metlin: J. Amer. Oil Chem. Soc. 44, 37 (1967).

    Article  CAS  Google Scholar 

  30. E. N. Frankel, G. P. Jones, Y. L. Davison, E. Emken, and H. J. Dutton: J. Amer. Oil Chem. Soc. 42, 130 (1965).

    Article  CAS  Google Scholar 

  31. R. H. Grubbs and T. K. Brunck: J. Amer. Chem. Soc. 94, 2538 (1972).

    Article  CAS  Google Scholar 

  32. P. Abley and F. J. McQuillin: J. Chem. Soc. Chem. Comm., 1503 (1969).

    Google Scholar 

  33. C. J. Love: Ph.D. Thesis, University of Newcastle upon Tyne, 1972, p. 38.

    Google Scholar 

  34. A. G. Hinze and D. J. Frost: J. Catal. 24, 540 (1972).

    Article  Google Scholar 

  35. H. Simon and O. Berngruber: Tetrahedron, 26, 161 (1970).

    Article  CAS  Google Scholar 

  36. M. St. Jaques and R. Prud’homme: Tetrahedron Letters, 4833 (1970).

    Google Scholar 

  37. D. Slack and M. C. Baird: J. Chem. Soc. Chem. Comm., 701 (1974).

    Google Scholar 

  38. D. Gaghaire and P. Voltero: Bull. Soc. chim. France, 164 (1970).

    Google Scholar 

  39. A. J. Birch and K. A. M. Walker: J. Chem. Soc. (C), 1894 (1966).

    Google Scholar 

  40. J. R. Morandi and H. B. Jensen: J. Org. Chem. 34, 1889 (1969).

    Article  CAS  Google Scholar 

  41. B. Zech, G. Jones, and C. Djerassi: Chem. Ber. 100, 3204 (1967).

    Article  Google Scholar 

  42. C. Djerassi and J. Gutzwiller: J. Amer. Chem. Soc. 88, 4537 (1966).

    Article  CAS  Google Scholar 

  43. H. J. Brodie, K. J. Kripalani, and G. Possanza: J. Amer. Chem. Soc. 91, 1241 (1969).

    Article  Google Scholar 

  44. B. Pelc and E. Kodicek: J. Chem. Soc. (C), 3415 (1971).

    Google Scholar 

  45. D. E. M. Lawson, B. Pelc, P. A. Bell, P. W. Wilson, and E. Kodicek: Biochem. J. 121, 673 (1971).

    CAS  Google Scholar 

  46. W. Yoelter and C. Djerassi: Chem. Ber. 101, 58 (1968).

    Article  Google Scholar 

  47. H. J. Brodie, C. E. Hay, and T. A. Willstruck: J. Org. Chem. 37, 3361 (1972).

    Article  CAS  Google Scholar 

  48. W. H. Fane, A. Failli, and C. Djerassi: J. Org. Chem. 35, 2571 (1970).

    Article  Google Scholar 

  49. B. Bayerl, M. Wahren, and J. Graefe: Tetrahedron 29, 1837 (1973).

    Article  CAS  Google Scholar 

  50. J. Sicher: Angew. Chem. Internat. Edn. 11, 200 (1972).

    Article  CAS  Google Scholar 

  51. E. N. Frankel, E. Selke, and C. A. Glass: J. Amer. Chem. Soc. 90, 2446 (1968).

    Article  CAS  Google Scholar 

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© 1976 D. Reidel Publishing Company, Dordrecht, Holland

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McQuillin, F.J. (1976). Isomerisation and Specific Deuteriation. In: Homogeneous Hydrogenation in Organic Chemistry. Homogeneous Catalysis in Organic and Inorganic Chemistry, vol 1. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-1878-4_7

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  • DOI: https://doi.org/10.1007/978-94-010-1878-4_7

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-1880-7

  • Online ISBN: 978-94-010-1878-4

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