Topics in Catalysis

, Volume 53, Issue 15–18, pp 1121–1125 | Cite as

Stereoselective Synthesis of Alicylic Amines

  • Kristoffer F. Graham
  • Kenneth T. Hindle
  • S. David Jackson
  • David J. M. Williams
  • Stefan Wuttke
Original Paper


The hydrogenation 4-alkylanilines over Rh/silica catalysts display an antipathetic particle size effect suggesting that the active site is a terrace face. The effect of the solvent on product cis:trans ratio was related to polar solvents stabilising an imine intermediate. The products inhibited the reaction due to their increased basicity which allowed a strong metal–nitrogen interaction.


Aromatic amine hydrogenation Rhodium Selectivity Deactivation 


  1. 1.
    Jackson SD, Hindle KT, Webb G (2005) In: Sowa J Jr (ed) Catalysis of organic reactions. Taylor & Francis, Boca Raton, pp 77–84Google Scholar
  2. 2.
    Jackson SD, Hindle KT, Stirling D, Webb G (2006) J Catal 241:417–425CrossRefGoogle Scholar
  3. 3.
    Hindle KT, Jackson SD, Webb G (2008) Curr Top Catal 7:115–125Google Scholar
  4. 4.
    van Hardeveld R, Hartog F (1972) Adv Catal 22:75CrossRefGoogle Scholar
  5. 5.
    Che M, Bennett CO (1989) Adv Catal 36:55CrossRefGoogle Scholar
  6. 6.
    Shore SG, Ding E, Park C, Keane MA (2002) Catal Commun 3:77CrossRefGoogle Scholar
  7. 7.
    Park C, Keane MA (2003) J Colloid Interface Sci 266:183–194CrossRefGoogle Scholar
  8. 8.
    Singh UK, Vannice MA (2001) Appl Catal A 213:1–24CrossRefGoogle Scholar
  9. 9.
    Gilbert L, Mercier CI (1993) Stud Surf Sci Catal 78:51CrossRefGoogle Scholar
  10. 10.
    Wehrli JT, Baiker AJ (1989) Mol Catal 57:245CrossRefGoogle Scholar
  11. 11.
    Blaser H-U, Jalett HP, Wiehl J (1991) J Mol Catal 68:215CrossRefGoogle Scholar
  12. 12.
    Augustine RL (1976) Adv Catal 25:56CrossRefGoogle Scholar
  13. 13.
    Wainwright MS, Ahn T, Trimm DL, Cant NW (1987) J Chem Eng Data 32:22–24CrossRefGoogle Scholar
  14. 14.
    Riazi MR, Roomi YA (2007) Chem Eng Sci 62:6649–6658CrossRefGoogle Scholar
  15. 15.
    Hindle KT (2003) Thesis, University of GlasgowGoogle Scholar
  16. 16.
    Singh UK, Krska SW, Sun Y (2006) Org Process Res Dev 10:1153–1156CrossRefGoogle Scholar
  17. 17.
    Griffin KG, Hawker S, Johnston P, Palacios M-L, Clayton C (1999) In: Morrell DG (ed) Catalysis of organic reactions. Marcel Dekker, Inc., New York, p 529Google Scholar
  18. 18.
    Xia D, Liu L, Huang M, Jiang Y (1999) Polym Adv Technol 10:116CrossRefGoogle Scholar
  19. 19.
    Greenfield HJ (1964) Org Chem 29:3082CrossRefGoogle Scholar
  20. 20.
    Pitara EL, N’Zemba B, Barbier J, Barbot F, Miginiac F (1996) J Mol Catal A 106:235CrossRefGoogle Scholar
  21. 21.
    Sokolskii DV, Ualikhanova A, Temirbulatova AE (1982) React Kinet Catal Lett 20:35CrossRefGoogle Scholar
  22. 22.
    Mink G, Horváth L (1998) React Kinet Catal Lett 65:59CrossRefGoogle Scholar
  23. 23.
    Freifelder M (1961) J Org Chem 26:1835CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Kristoffer F. Graham
    • 1
  • Kenneth T. Hindle
    • 1
  • S. David Jackson
    • 1
  • David J. M. Williams
    • 1
  • Stefan Wuttke
    • 1
  1. 1.Centre for Catalysis Research, WestCHEM, Department of ChemistryUniversity of GlasgowGlasgowScotland, UK

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