General acid catalysed hydrolysis of β-sultams involves nucleophilic catalysis

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Nicholas J. Baxter, Andrew P. Laws, Laurent J. H. Rigoreau and Michael I. Page


Abstract

The hydrolysis of the four-membered ring sulfonamide N-benzyl β-sultam is catalysed by carboxylic acids, which is attributed to specific acid–nucleophilic catalysis with the intermediate formation of a mixed anhydride which can be trapped with aniline.


References

  1. A. P. Laws, J. R. Stone and M. I. Page, J. Chem. Soc., Chem. Commun., 1994, 1223 RSC.
  2. N. J. Baxter, A. P. Laws, L. Rigoreau and M. I. Page, J. Chem. Soc., Perkin Trans. 2, 1996, 2245 RSC.
  3. H. Maskill, Chem. Soc. Rev., 1989, 18, 123 RSC; A. J. Buglass and J. G. Tillett, The Chemistry of Sulphonic Acids, Esters and their Derivatives, ed. S. Patai and Z. Rappoport, Wiley, Chichester, UK, 1991, ch. 19 Search PubMed.
  4. W. J. Moree, A. Schouten, J. R. Kroon and R. M. V. Liskamp, Int. J. Pept. Protein Res., 1995, 45, 501 CAS.
  5. A. M. Davis, P. Proctor and M. I. Page, J. Chem. Soc., Perkin Trans. 2, 1991, 1213 RSC.
  6. R. G. Laughlin, J. Am. Chem. Soc., 1967, 89, 4268 CrossRef CAS; F. M. Menger and L. Mandell, J. Am. Chem. Soc., 1967, 89, 4424 CrossRef CAS.
  7. Y. Bekdemir, J. G. Tillett and R. I. Zalewski, J. Chem. Soc., Perkin Trans. 2, 1993, 1643 RSC; D. Klamann and G. Hofbauer, Liebigs Ann. Chem., 1953, 581, 182 Search PubMed; D. Klamann and E. Fabienka, Chem. Ber., 1959, 712 CAS; W. F. Erman and J. C. Kretschmar, J. Am. Chem. Soc., 1961, 83, 4841.
  8. P. Proctor, N. P. Gensmantel and M. I. Page, J. Chem. Soc., Perkin Trans. 2, 1982, 1185 RSC.
  9. M. I. Page, A. P. Laws, M. J. Slater and J. R. Stone, Pure Appl. Chem., 1995, 67, 711 CAS.
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