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DOI: 10.1039/A905498G (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 2771-2782

Synthesis of cyclic ethers and allylic sulfides by rearrangement of phenylsulfanyl substituted 1,n-diols with toluene-p-sulfonic acid and with toluene-p-sulfonyl chloride

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Laurent Djakovitch, Jason Eames, David J. Fox, Francis H. Sansbury and Stuart Warren

Abstract

Rearrangement of a series of 1,n-diols (n = 2 to 12), with a PhS-group adjacent to one OH group, under two sets of conditions gives single compounds in excellent yield drawn for four possible classes of products. The effect of the chain length helps in the understanding of the different cyclisation modes and the mechanism of the rearrangements.

References

  1. P. Brownbridge and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1977, 2272 RSC.
  2. V. K. Aggarwal and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1987, 2579 RSC.
  3. V. K. Aggarwal and S. Warren, Tetrahedron Lett., 1986, 27, 101 CrossRef CAS.
  4. V. K. Aggarwal, I. Coldham, S. McIntye and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1991, 451 RSC.
  5. I. Coldham and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1993, 1637 RSC.
  6. (a) J. Eames, R. V. H. Jones and S. Warren, Tetrahedron Lett., 1996, 37, 707 CrossRef CAS; (b) J. Eames and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1999, 2783 RSC.
  7. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734 RSC.
  8. (a) A. J. Kirby, Adv. Phys. Org. Chem., 1981, 17, 183; (b) L. Mandolini, Adv. Phys. Org. Chem., 1986, 22, 1 CAS.
  9. (a) F. H. Sansbury and S. Warren, Tetrahedron Lett., 1991, 32, 3425 CrossRef CAS; (b) S. McIntyre, F. H. Sansbury and S. Warren, Tetrahedron Lett., 1991, 32, 5409 CrossRef CAS; (c) F. H. Sansbury and S. Warren, Tetrahedron Lett., 1992, 33, 539 CrossRef CAS.
  10. Inversion also occurs at the migratory origin, see V. K. Aggarwal, I. Coldham, S. McIntye, F. H. Sansbury, M.-J. Villa and S. Warren, Tetrahedron Lett., 1988, 29, 4885 Search PubMed.
  11. J. Eames and S. Warren, Tetrahedron Lett., 1996, 37, 3525 CrossRef CAS.
  12. Preliminary communication: L. Djakovitch, J. Eames, R. V. H. Jones, S. McIntyre and S. Warren, Tetrahedron Lett., 1995, 36, 1723 Search PubMed.
  13. J. Eames, H. J. Mitchell, A. Nelson, P. O'Brien, S. Warren and P. Wyatt, Tetrahedron Lett., 1995, 36, 1719 CrossRef CAS.
  14. J. Eames, H. J. Mitchell, A. Nelson, P. OBrien, S. Warren and P. Wyatt, J. Chem. Soc., Perkin. Trans. 1, 1999, 1095 RSC.
  15. P. Brownbridge and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1977, 1131 RSC.
  16. J. Eames, Ph.D. Thesis, University of Cambridge, 1996.
  17. E. J. Corey and M. J. Chaykovsky, J. Am. Chem. Soc., 1965, 87, 1353 CrossRef CAS.
  18. J. Eames, M. A. de las Heras, R. V. H. Jones and S. Warren, Tetrahedron Lett., 1996, 37, 1117 CrossRef CAS.
  19. E. L. Eliel, W. H. Pearson, L. M. Jewell, A. G. Abatjoglou and W. R. Kenan, Tetrahedron Lett., 1980, 21, 331 CrossRef CAS.
  20. P. C. Eaton, G. F. Cooper, R. C. Johnson and R. H. Muellur, J. Org. Chem., 1972, 37, 1947 CrossRef CAS.
  21. J. Eames, N. Kuhnert, F. H. Sansbury and S. Warren, Synlett, 1999, 1211 CAS.
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