Mild, efficient cleavage of arenesulfonamides by magnesium reduction

(Note: The full text of this document is currently only available in the PDF Version )

Barthélémy Nyasse, Leif Grehn and Ulf Ragnarsson


Abstract

The cleavage of arenesulfonamides via N-arenesulfonylcarbamates is achieved within a few minutes under ultrasonic conditions by reaction with magnesium in anhydrous methanol.


References

  1. (a) T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Chemistry, Wiley-Interscience, New York, 2nd edn., 1991 Search PubMed; (b) P. J. Kocienski, Protecting Groups, Thieme, New York, 1994 Search PubMed.
  2. J. R. Henry, L. R. Marcin, M. C. McIntosh, P. M. Scola, G. D. Harris and S. M. Weinreb, Tetrahedron Lett., 1989, 30, 5709 CrossRef CAS.
  3. R. C. Roemmele and H. Rapaport, J. Org. Chem., 1988, 53, 2367 CrossRef CAS and references cited therein.
  4. S. Ji, L. B. Gortler, A. Waring, A. Battisti, S. Bank, W. D. Closson and P. Wriede, J. Am. Chem. Soc., 1967, 89, 5311 CrossRef CAS.
  5. (a) E. Vedejs and S. Lin, J. Org. Chem., 1994, 59, 1602 CrossRef CAS; (b) C. Goulaouic-Dubois, A. Guggisberg and M. Hesse, J. Org. Chem., 1995, 60, 5969 CrossRef CAS; (c) C. Goulaouic-Dubois, A. Guggisberg and M. Hesse, Tetrahedron, 1995, 51, 12 573 CrossRef CAS; (d) E. Vedejs, S. Lin, A. Klapars and J. Wang, J. Am. Chem. Soc., 1996, 118, 9796 CrossRef CAS.
  6. A. F. Parsons and R. M. Pettifer, Tetrahedron Lett., 1996, 37, 1667 CrossRef CAS.
  7. (a) B. Nyasse, L. Grehn, U. Ragnarsson, H. L. S. Maia, L. S. Monteiro, I. Leito, I. Koppel and J. Koppel, J. Chem. Soc., Perkin Trans. 1, 1995, 2025 RSC and references cited therein; (b) L. Grehn, K. Gunnarsson and U. Ragnarsson, Acta Chem. Scand., Ser. B, 1986, 40, 745 Search PubMed.
  8. O. Nishimura and M. Fujino, Chem. Pharm. Bull., 1976, 24, 1568 CAS.
  9. R. Ramage, J. Green and A. J. Blake, Tetrahedron, 1991, 47, 6353 CrossRef CAS.
  10. A. C. Brown and L. A. Carpino, J. Org. Chem., 1985, 50, 1749 CrossRef CAS.
  11. G. H. Lee, E. B. Choi, E. Lee and C. S. Pak, Tetrahedron Lett., 1993, 34, 4541 CrossRef CAS.
  12. Y. Yokoyama, T. Matsumoto and Y. Murakami, J. Org. Chem., 1995, 60, 1486 CrossRef CAS.
  13. R. O. Hutchins, Suchismita, R. E. Zipkin and I. M. Taffer, Synth. Commun., 1989, 19, 1519 CAS.
  14. A. Zarecki and J. Wicha, Synthesis, 1996, 455 CrossRef CAS.
  15. L. Grehn, K. Gunnarsson and U. Ragnarsson, Acta Chem. Scand., Ser. B, 1987, 41, 18 Search PubMed.