Reactions of Carbonyl Compounds

  • Francis A. Carey
  • Richard J. Sundberg

Abstract

The carbonyl group is one of the most prevalent of the functional groups; great importance is therefore attached both to mechanistic studies and synthetic processes involving carbonyl compounds. Reactions involving carbonyl groups are also exceptionally important in biological processes. Most of the reactions of aldehydes, ketones, esters, amides, and other carboxylic acid derivatives are intimately associated with the carbonyl group. In Chapter 7, the role of the carbonyl group in stabilizing carbanion centers was discussed. The first two chapters of Part B deal mainly with the chemistry of carbonyl compounds, reflecting their importance in formation of carbon—carbon bonds in organic synthesis. In this chapter, the primary topic for discussion will be the characteristic mechanistic patterns of reactions at carbonyl centers.

Keywords

Proton Transfer Carbonyl Compound Alkoxy Group Ester Hydrolysis Tetrahedral Intermediate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

General References

  1. W. P. Jencks, Catalysis in Chemistry and Enzymology, McGraw-Hill, New York, 1969.Google Scholar
  2. M. L. Bender, Mechanisms of Homogeneous Catalysis from Protons to Proteins, Wiley—Interscience, New York, 1971.Google Scholar
  3. T. C. Bruice and S. J. Benkovic, Bioorganic Mechanisms, Benjamin, New York, 1966.Google Scholar
  4. A. J. Kirby and A. R. Fersht, in Progress in Bioorganic Chemistry, Vol. 1, E. T. Kaiser and F. J. Kezdy (eds.), Wiley-Interscience, New York, 1971, pp. 1–82.Google Scholar
  5. S. Patai (ed.), The Chemistry of the Carbonyl Group, Wiley-Interscience, New York, 1974.Google Scholar
  6. S. Patai (ed.), The Chemistry of Carboxylic Acids and Esters, Wiley-Interscience, New York, 1969.Google Scholar
  7. J. E. Zabicky (ed.), The Chemistry of Amides, Wiley-Interscience, New York, 1970.Google Scholar

Chapter 8

  1. 1.
    R. P. Bell, Adv. Phys. Org. Chem. 4, 1 (1966).CrossRefGoogle Scholar
  2. 2a.
    A. Lapworth and R. H. F. Manske, J. Chem. Soc. 1976 (1930).Google Scholar
  3. b.
    T. H. Fife, J. E. C. Hutchins, and M. S. Wang, J. Am. Chem. Soc. 97, 5878 (1975).CrossRefGoogle Scholar
  4. c.
    K. Bowden and A. M. Last, Chem. Commun. 1315 (1970).Google Scholar
  5. d.
    P. R. Young and W. P. Jencks, J. Am. Chem. Soc. 99, 1206 (1977).CrossRefGoogle Scholar
  6. 3a,b.
    M. M. Kreevoy and R. W. Taft, Jr., J. Am. Chem. Soc. 77, 5590 (1955).CrossRefGoogle Scholar
  7. c,d.
    M. M. Kreevoy, C. R. Morgan, and R. W. Taft, Jr., J. Am. Chem. Soc. 82, 3064 (1960).CrossRefGoogle Scholar
  8. e.
    T. H. Fife and L. H. Brod, J. Org. Chem. 33, 4136 (1968).CrossRefGoogle Scholar
  9. 4.
    R. G. Bergstrom, M. J. Cashen, Y. Chiang, and A. J. Kresge, J. Org. Chem. 44, 1639 (1979).CrossRefGoogle Scholar
  10. 5a.
    T. Maugh, II and T. C. Bruice, J. Am. Chem. Soc. 93, 3237 (1971).CrossRefGoogle Scholar
  11. b.
    L. E. Eberson and L.-Å. Svensson, J. Am. Chem. Soc. 93, 3827 (1971).CrossRefGoogle Scholar
  12. c.
    A. Williams and G. Salvadori, J. Chem. Soc. Perkin Trans. II 883 (1972).Google Scholar
  13. d.
    G. A. Rogers and T. C. Bruice, J. Am. Chem. Soc. 96, 2463 (1974).CrossRefGoogle Scholar
  14. e.
    K. Bowden and G. R. Taylor, J. Chem. Soc. B 145, 149 (1971);CrossRefGoogle Scholar
  15. M. S. Newman and A. L. Leegwater, J. Am. Chem. Soc. 90, 4410 (1968).CrossRefGoogle Scholar
  16. f.
    T. C. Bruice and S. J. Benkovic, J. Am. Chem. Soc. 85, 1 (1963).CrossRefGoogle Scholar
  17. 6.
    E. H. Cordes and W. P. Jencks, J. Am. Chem. Soc. 85, 2843, (1963).CrossRefGoogle Scholar
  18. 7.
    E. Anderson and T. H. Fife, J. Am. Chem. Soc. 95, 6437 (1973).CrossRefGoogle Scholar
  19. 8.
    M. W. Williams and G. T. Young, J. Chem. Soc., 3701 (1964).Google Scholar
  20. 9.
    R. Breslow and C. McAllister, J. Am. Chem. Soc. 93, 7096 (1971).CrossRefGoogle Scholar
  21. 10.
    B. Capon and K. Nimmo, J. Chem. Soc., Perkin Trans. II, 1113 (1975).Google Scholar
  22. 11.
    H. R. Mahler and E. H. Cordes, Biological Chemistry, Harper and Row, New York, 1966, p. 201.Google Scholar
  23. 12.
    J. Hajdu and G. M. Smith, J. Am. Chem. Soc. 103, 6192 (1981).CrossRefGoogle Scholar
  24. 13.
    T. Okuyama, H. Shibuya, and T. Fueno, J. Am. Chem. Soc. 104, 730 (1982).CrossRefGoogle Scholar
  25. 14.
    R. P. Bell, M. H. Rand, and K. M. A. Wynne-Jones, Trans. Faraday Soc. 52, 1093 (1956).CrossRefGoogle Scholar
  26. 15.
    J. Hine, M. S. Cholod, and W. K. Chess, Jr., J. Am. Chem. Soc. 95, 4270 (1973).CrossRefGoogle Scholar
  27. 16.
    J. T. Edward and S. C. Wong, J. Am. Chem. Soc. 101, 1807 (1979).CrossRefGoogle Scholar
  28. 17.
    A. J. Kirby and P. W. Lancaster, J. Chem. Soc., Perkin Trans. II, 1206 (1972).Google Scholar
  29. 18a.
    T. C. Bruice and I. Oka, J. Am. Chem. Soc. 96, 4500 (1974).CrossRefGoogle Scholar
  30. b.
    R. Hershfield and G. L. Schmir, J. Am. Chem. Soc. 95, 7359 (1973).CrossRefGoogle Scholar
  31. c.
    T. H. Fife and J. E. C. Hutchins, J. Am. Chem. Soc. 94, 2837 (1972).CrossRefGoogle Scholar
  32. d.
    J. Hine, J. C. Craig, Jr., J. G. Underwood, II, and F. A. Via, J. Am. Chem. Soc. 92, 5194 (1970).CrossRefGoogle Scholar
  33. 19.
    D. P. Weeks and D. B. Whitney, J. Am. Chem. Soc. 103, 3555 (1981).CrossRefGoogle Scholar
  34. 20.
    R. L. Schowen, C. R. Hopper, and C. M. Bazikian, J. Am. Chem. Soc. 94, 3095 (1972).CrossRefGoogle Scholar
  35. 21.
    E. Tapuhi and W. P. Jencks, J. Am. Chem. Soc. 104, 5758 (1982).CrossRefGoogle Scholar
  36. 22.
    C. M. Evans, R. Glenn, and A. J. Kirby, J. Am. Chem. Soc. 104, 4706 (1982).CrossRefGoogle Scholar
  37. 23.
    E. H. Cordes and W. P. Jencks, J. Am. Chem. Soc. 85, 2843 (1963).CrossRefGoogle Scholar
  38. 24.
    T. S. Davies, P. D. Feil, D. G. Kubler, and D. J. Wells, Jr., J. Org. Chem. 40, 1478 (1975).CrossRefGoogle Scholar
  39. 25.
    L. doAmaral, M. P. Bastos, H. G. Bull, and E. H. Cordes, J. Am. Chem. Soc. 95, 7369 (1973).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1984

Authors and Affiliations

  • Francis A. Carey
    • 1
  • Richard J. Sundberg
    • 1
  1. 1.University of VirginiaCharlottesvilleUSA

Personalised recommendations