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DOI: 10.1039/A801322E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 1333-1338

Two pathways for the stereomutation of 2-substituted 1-(tert-butylsulfinyl)naphthalenes

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Robert W. Baker, Rekha V. Kyasnoor and Melvyn V. Sargent

Abstract

The synthesis of a number of 2-substituted 1-(tert-butylsulfinyl)naphthalenes is described and the free energies of activation (ΔG[hair space] ‡ = 50.0–80.7 kJ mol–1) for their stereomutation about the S–Ar bonds have been determined. It is shown that two pathways operate for this process. For the smaller 2-substituents (F, OMe, CO2Pri), the tert-butyl group passes over the 2-position, and for larger substituents (Cl, Me, Br) it passes over the 8-position of the naphthalene ring.

References

  1. W. H. Mills and K. A. C. Elliot, J. Chem. Soc., 1928, 1291 RSC.
  2. R. Kuhn and P. Goldfinger, Liebigs Ann. Chem., 1929, 470, 183 Search PubMed.
  3. R. W. Baker, D. C. R. Hockless, G. R. Pocock, M. V. Sargent, B. W. Skelton, A. N. Sobolev, E. Twiss and A. H. White, J. Chem. Soc., Perkin Trans. 1, 1995, 2615 RSC.
  4. D. Casarini, E. Foresti, F. Gasparrini, L. Lunazzi, D. Macciantelli, D. Misiti and C. Villani, J. Org. Chem., 1993, 58, 5674 CrossRef CAS.
  5. R. Lett and A. Marquet, Tetrahedron, 1974, 30, 3379 CrossRef CAS.
  6. W. B. Jennings, M. Kochanewycz and L. Lunazzi, J. Chem. Soc., Perkin Trans. 2, 1997, 2271 RSC.
  7. T. Migita, T. Shimuzu, Y. Asami, F. Shiobara, Y. Kato and M. Kosugi, Bull. Chem. Soc. Jpn., 1980, 53, 1385 CAS.
  8. G. W. Gribble, C. S. LeHoullier, R. W. Allen and J. J. Gilbertson, Org. Prep. Proced. Int., 1981, 13, 349 CAS.
  9. C. A. Kingsbury and D. A. Cram, J. Am. Chem. Soc., 1960, 82, 1810 CrossRef.
  10. J. Sandström, Dynamic NMR Spectroscopy, Academic Press, London, 1982 Search PubMed; M. Ōki, Application of Dynamic NMR Spectroscopy to Organic Chemistry, VCH, Weinheim, 1985 Search PubMed.
  11. G. Binsch and H. Kessler, Angew. Chem., Int. Ed. Engl., 1980, 19, 411 CrossRef; R. B. Palmer and N. H. Andersen, Tetrahedron, 1996, 52, 9665 CrossRef CAS.
  12. G. Bott, L. D. Field and S. Sternhell, J. Am. Chem. Soc., 1980, 102, 5618 CrossRef CAS.
  13. B. Sket, P. Zupetz and M. Zupan, J. Chem. Soc., Perkin Trans. 1, 1989, 2279 RSC.
  14. G. Moses and E. E. Reid, J. Am. Chem. Soc., 1926, 48, 776 CrossRef.
  15. D. R. Coulson, Inorg. Synth., 1972, 13, 121.
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