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Feist’s Acid

  • Douglas Lloyd

Abstract

Although Feist’s Acid is a small molecule with molecular formula C6H6O4, almost sixty years passed from its first preparation before its correct structure was elucidated. The unfolding of the story makes an entertaining historical study while the authenticated properties of this compound are also of much interest. Perhaps most surprising is its considerable stability, in view of the large steric strain which must be anticipated for the molecule, but samples remain unchanged for many years.

Keywords

Dimethyl Ester Diethyl Ester Hydriodic Acid Phosphorus Pentachloride Lithium Aluminium Hydride 
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.

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References

  1. Blomquist, A. T. and Longone, D. T. (1959) J. Amer. Chem. Soc. 81, 2012.CrossRefGoogle Scholar
  2. Boreham, g. R., Goss, F. R. and Minkoff, G. J. (1955) Chewy. Ind. 1354.Google Scholar
  3. Bottini, A. T. and Davidson, A. J. (1965) J. Org. Chem. 30, 3302.CrossRefGoogle Scholar
  4. Bottini, A. T. and Roberts, J. D. (1956) J. Org. Chem. 21, 1169.Google Scholar
  5. Buchner, E. and Schroder, H. (1902) Ber. 35, 782.Google Scholar
  6. Carbon, J. A., Martin, W. B. and Swett, L. R. (1958) J. Amer. Chem. Soc. 80, 1002.CrossRefGoogle Scholar
  7. Cheswick, J. P. (1963) J. Amer. Chem. Soc. 85, 2720.CrossRefGoogle Scholar
  8. Dorko, E. A. (1965) J. Amer. Chem. Soc. 87, 5518.CrossRefGoogle Scholar
  9. Downie, T. C. (1952) Ph.D. Thesis, University of Glasgow.Google Scholar
  10. Downie, T. C. and Speakman, J. C. (1954) Acta Cryst. 7, 647.Google Scholar
  11. Erickson, R. E. (1966) Tetrahedron Letters 1753.Google Scholar
  12. Ettlinger, M. G. (1952) J. Amer. Chem. Soc. 74, 5808.CrossRefGoogle Scholar
  13. Ettlinger, M. G., Harper, S. H. and Kennedy, F. (1957) J. Chem. Soc. 922.Google Scholar
  14. Ettlinger, M. G. and Kennedy, F. (1956) Chewy. Ind. 166.Google Scholar
  15. Ettlinger, M. G. and Kennedy, F. (1957) Chemy. Ind. 891.Google Scholar
  16. Feist, F. (1893) Ber. 26. 747.Google Scholar
  17. Feist, F. (1906) Liebigs Ann. 345, 103.Google Scholar
  18. Feist, F. (1924) Liebigs Ann. 436, 125.CrossRefGoogle Scholar
  19. Gilchrist, T. L. (1964) Ph.D. Thesis, University of London.Google Scholar
  20. Gilchrist, T. L. and Rees, C. W. (1968a) J. Chem. Soc. (C) 769.Google Scholar
  21. Gilchrist, T. L. and Rees, C. W. (1968b) J. Chem. Soc. (C) 776.Google Scholar
  22. Goss, F. R. and Ingold, C. K. (1925) J. Chem. Soc. 127, 2776.CrossRefGoogle Scholar
  23. Goss, F. R. and Ingold, C. K. (1928) J. Chem. Soc. 1268.Google Scholar
  24. Goss, F. R., Ingold, C. K. and Thorpe, J. F. (1923a) J. Chem. Soc. 123, 327.CrossRefGoogle Scholar
  25. Goss, F. R., Ingold, C. K. and Thorpe, J. F. (1923b) J. Chem. Soc. 123, 3342.CrossRefGoogle Scholar
  26. Goss, F. R., Ingold, C. K. and Thorpe, J. F. (1925) J. Chem. Soc. 127, 460.CrossRefGoogle Scholar
  27. Gragson, J. T., Greenlee, K. W., Derfer, J. M. and Boord, C. E. (1953) J. Amer. Chem. Soc. 75, 3344.CrossRefGoogle Scholar
  28. Graham, J. D. and Rogers, M. T. (1962) J. Amer. Chem. Soc. 84, 2249.CrossRefGoogle Scholar
  29. Ingold, C. K. (1922) J. Chem. Soc. 121, 2676.CrossRefGoogle Scholar
  30. Jones, D. T. (1905) J. Chem. Soc. 87, 1062.CrossRefGoogle Scholar
  31. Kende, A. S. (1956) Chemy. Ind. 437, 544.Google Scholar
  32. Kon, G. A. R. and Nanji, H. R. (1932) J. Chem. Soc. 2557.Google Scholar
  33. Lemieux, R. U. and Rudloff, E. von (1955) Canad. J. Chem. 33, 1701, 1710.CrossRefGoogle Scholar
  34. Liebermann, D., Rist, N., Grumbach, F., Moyeux, M., Gauthier, B., Rouaix, A., Maillard, J., Himbert, J. and Cals, S. (1954) Bull. soc. chim. France 1430.Google Scholar
  35. Lloyd, D. unpublished work.Google Scholar
  36. Lloyd, D., Downie, T. C. and Speakman, J. C. (1954a) Chemy. Ind. 222.Google Scholar
  37. Lloyd, D., Downie, T. C. and Speakman, J. C. (1954b) Chemy. Ind. 492.Google Scholar
  38. Lloyd, D. and Mmie, J. F. W. (1956) Chemy. Ind. 874.Google Scholar
  39. Lowry, T. M. and Burgess, H. (1923) J. Chem. Soc. 123, 2111.CrossRefGoogle Scholar
  40. Petersen, D. R. (1956) Chemy. Ind. 904.Google Scholar
  41. Schwan, U. (1958) Dissertation, Tech. Hoch., Karlsruhe.Google Scholar
  42. Ullman, E. F. (1959) J. Amer. Chem. Soc. 81, 5386.CrossRefGoogle Scholar
  43. Ullman, E. F. (1960) J. Amer. Chem. Soc. 82, 505.CrossRefGoogle Scholar
  44. Ullman, E. F. and Fanshawe, W. J. (1961) J. Amer. Chem. Soc. 83, 2379.CrossRefGoogle Scholar

Copyright information

© Logos Press Limited 1969

Authors and Affiliations

  • Douglas Lloyd
    • 1
  1. 1.Department of Chemistry, United College of St. Salvator and St. LeonardUniversity of St. AndrewsUK

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