Photodegradation of aryl sulfonamides: N-tosylglycine

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Roger R. Hill, Graham E. Jeffs, David R. Roberts and Sharon A. Wood


Abstract

Continuing uncertainty about pathways and consequences of the photolability of aryl sulfonamides is partly resolved by the results of comprehensive product analysis in the photolysis of aqueous N-tosylglycine, which indicate that intramolecular electron or hydrogen transfer (according to conditions) promote the widely reported S–N cleavage and reveal the nature of subsequent and competing processes.


References

  1. (a) Drugs: Photochemistry and Photostability, ed. A. Albini and E. Fasani, Royal Society of Chemistry, London, 1998 Search PubMed; (b) Photostability of Drugs and Drug Formulations, ed. H. H. Tonnesen, Taylor and Francis, London, 1996 Search PubMed.
  2. G. Papageorgiou and J. E. T. Corrie, Tetrahedron, 1999, 55, 237 CrossRef CAS.
  3. J. A. Pincock, in Handbook of Photochemistry and Photobiology, ed. W. M. Horsepool and P.-S. Song, CRC Press, Boca Raton, 1995, p. 757 Search PubMed; J. E. T. Corrie and G. Papageorgiou, J. Chem. Soc., Perkin Trans. 1, 1996, 1583 Search PubMed.
  4. L. D'Souza, Science, 1968, 160, 882 CAS.
  5. Ref. 1(a), p. 66.
  6. T. Hamada, A. Nishida and O. Yonemitsu, Tetrahedron Lett., 1989, 30, 4241 CrossRef CAS.
  7. R. R. Hill, J. D. Coyle, D. Birch, E. Dawe, G. E. Jeffs, D. Randall, I. Stec and T. M. Stevenson, J. Am. Chem. Soc., 1991, 113, 1805 CrossRef CAS.
  8. R. R. Hill, C. W. Richenberg and D. R. Roberts, J. Photochem. Photobiol.A: Chem., 1996, 97, 109 CrossRef CAS; R. R. Hill, G. E. Jeffs, F. Banaghan, T. McNally and A. R. Werninck, J. Chem. Soc., Perkin Trans. 2, 1996, 1595 RSC.
  9. Waters Millenium System with diode array detection; Phenomenex Luna 5 mm C18 column; gradient elution using water, 0.1 mol dm–3 phosphoric acid and MeCN.
  10. C. van Wandelen and S. A. Cohen, J. Chromatogr., 1997, 763, 11 CrossRef CAS.
  11. G. Sieler, R. Schweitzer-Sterner, J. S. W. Holtz, V. Pajcini and S. A. Asher, J. Phys. Chem. B, 1999, 103, 372 CrossRef CAS; C. M. Brenemen and L. W. Weber, Can. J. Chem., 1996, 74, 1271.
  12. G. Jones, L. N. Lu, H. Fu, C. W. Farahat, C. Oh, S. R. Greenfield, D. J. Gosztola and M. R. Wasielewski, J. Phys. Chem. B, 1999, 103, 572 CrossRef.
  13. Closely analogous to that observed in the photolytic decarboxylation of phthalimido amino acids: A. G. Griesbeck, Chimia, 1998, 52, 272 Search PubMed.
  14. R. Kossai, B. Emir, J. Simonet and G. Mousset, J. Electroanal. Chem., 1989, 270, 253 CrossRef CAS.
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