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DOI: 10.1039/A808356H (Paper) Reference Section for: Chem. Commun., 1999, 189-190

Preparation, characterisation and slow quantitative dissociation of a novel asymmetric N-unsubstituted dialkylsulfimide

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Anthony D. M. Curtis, Christopher A. Ramsden, Muhammad R. Raza and Ray McCague

Abstract

(±)-S-Imino-4,5-dihydro-3H-dinaphtho[2,1-c:1′,2′-e]thiepine, a novel asymmetric N-unsubstituted sulfimide, undergoes slow, quantitative N–S bond cleavage in CDCl3 solution at 20 oC with a half-life of 20 h.

References

  1. J. I. Musher, Angew. Chem., Int. Ed., Engl., 1969, 8, 54 CrossRef CAS; C. A. Ramsden, Chem. Soc. Rev., 1994, 23, 111 RSC.
  2. 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley-Inter-science, New York, 1984 Search PubMed.
  3. A. Varvoglis, Hypervalent Iodine Chemistry in Organic Synthesis, Academic Press, London, 1997 Search PubMed.
  4. R. M. Moriarty, R. K. Vaid and G. F. Koser, Synlett, 1990, 365 CrossRef CAS.
  5. N. Furukawa, T. Omata, T. Yoshimura, T. Aida and S. Oae, Tetrahedron Lett., 1972, 1619 CrossRef CAS.
  6. T. Yoshimura, T. Omata, N. Furukawa and S. Oae, J. Org. Chem., 1976, 41, 1728 CrossRef CAS.
  7. S. Oae and N. Furukawa, Sulfilimines and Related Derivatives, ACS Monograph 179, American Chemical Society, Washington, DC, 1983 Search PubMed.
  8. R. Appel and W. Büchner, Chem. Ber., 1962, 95, 2220 CAS; R. Appel and W. Büchner, Angew. Chem., Int. Ed. Engl., 1959, 71, 701 Search PubMed; R. Appel, W. Büchner and E. Guth, Liebigs Ann. Chem., 1958, 618, 53 Search PubMed.
  9. J. B. Lambert, C. E. Mixan and D. S. Bailey, J. Am. Chem. Soc., 1972, 94, 208 CrossRef CAS.
  10. C. A. Ramsden and H. L. Rose, J. Chem. Soc., Perkin Trans. 1, 1997, 2319 RSC.
  11. I. G. Stará, I. Stary, M. Tichy, J. Závada and P. Fiedler, J. Org. Chem., 1994, 59, 1326 CrossRef CAS.
  12. Y. Tamura, J. Minamikawa and M. Ikeda, Synthesis, 1977, 1 CrossRef CAS.
  13. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902 CrossRef.
  14. M. J. S. Dewar, The Molecular Orbital Theory of Organic Chemistry, McGraw-Hill, New York, 1969, p. 284 Search PubMed.
  15. G. Besenyei, S. Németh and L. I. Simándi, Tetrahedron Lett., 1993, 6105 CrossRef CAS.
  16. R. C. Belloli and V. A. LaBahn, J. Org. Chem., 1975, 40, 1972 CrossRef CAS; R. C. Belloli, M. A. Whitehead, R. H. Wollenberg and V. A. LaBahn, J. Org. Chem., 1974, 39, 2128 CrossRef CAS; G. R. Felt, S. Linke and W. Lwowski, Tetrahedron Lett., 1972, 2037 CrossRef CAS; D. S. Breslow and E. I. Edwards, Tetrahedron Lett., 1972, 2041 CrossRef CAS.
  17. R. Gleiter and R. Hoffmann, Tetrahedron, 1968, 24, 5899 CrossRef CAS.
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