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DOI: 10.1039/A804605K (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 3059-3064

Chemical transformations of solvent-derived ozonolysis products: acid-catalysed reactions of α-alkoxy α′-hydroperoxy isochromans with aldehydes

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Kevin J. McCullough, Yoshihiro Ushigoe, Shogo Tanaka, Shin-ichi Kawamura, Araki Masuyama and Masatomo Nojima

Abstract

α-(2,2,2-Trifluoroethoxy) α′-hydroperoxy cyclic ethers 6, derived from the ozonolysis of 1-substituted indenes in 2,2,2-trifluoroethanol, undergo acid-catalysed cyclocondensations with aliphatic aldehydes to yield 1,2,4,6-tetroxepanes 8. With formaldehyde, hydroperoxides 6 afford the structurally novel 1,2,4,6,8-pentoxonane derivatives 9 in addition to 1,2,4,6-tetroxepanes. In contrast, the analogous acid-catalysed cyclocondensations involving the isomeric hydroperoxides 7 result in extensive degradation, though acidolysis of hydroperoxides 7 gives rise to the symmetrical 1,2-dialkyl peroxides 16.

References

  1. (a) Ozonation in Organic Chemistry, ed. P. S. Bailey, Academic Press, New York, 1978, vol. 1; 1982, vol. 2 Search PubMed; (b) The Chemistry of Peroxides, ed. S. Patai, Wiley, New York, 1983 Search PubMed.
  2. K. J. McCullough and M. Nojima, in Organic Peroxides, ed. W. Ando, Wiley, New York, 1992, pp. 661–728 Search PubMed.
  3. (a) D. A. Casteel, Nat. Prod. Rep., 1992, 9, 290 Search PubMed; (b) K. J. McCullough, Contemp. Org. Synth., 1995, 2, 225 RSC.
  4. K. J. McCullough, Y. Ushigoe, S. Tanaka, A. Masuyama and M. Nojima, J. Chem. Soc., Perkin Trans. 1, 1998, 3053 RSC.
  5. K. Teshima, S. Kawamura, Y. Ushigoe, M. Nojima and K. J. McCullough, J. Org. Chem., 1995, 60, 4755 CrossRef CAS.
  6. Y. Ushigoe, S. Tanaka, M. Nojima and K. J. McCullough, Tetrahedron Lett., 1994, 35, 9741 CrossRef CAS.
  7. (a) A. J. Bloodworth and A. Shah, J. Chem. Soc., Chem. Commun., 1991, 947 RSC; (b) A. J. Bloodworth and N. A. Tallant, J. Chem. Soc., Chem. Commun., 1992, 428.1 RSC.
  8. J. C. Bevington, Quart. Rev. Chem. Soc., 1952, 6, 141 Search PubMed.
  9. M. Schulz and K. Kirschke, ‘Organic Peroxides’ Vol III, ed. D. Swern, Wiley, New York, 1972, pp. 67–140 Search PubMed.
  10. Y. Ushigoe, S. Kawamura, K. Teshima, M. Nojima and K. J. McCullough, Tetrahedron Lett., 1996, 37, 2093 CrossRef CAS.
  11. (a) A. Rieche and E. Schmitz, Chem. Ber., 1957, 90, 1082 CAS; (b) A. Rieche and M. Schulz, Justus Liebigs Ann. Chem., 1962, 653, 32 CAS.
  12. (a) T. Sugimoto, M. Nojima, S. Kusabayashi and K. J. McCullough, J. Am. Chem. Soc., 1990, 112, 3690 CrossRef CAS; (b) K. J. McCullough, T. Sugimoto, S. Tanaka, S. Kusabayashi and M. Nojima, J. Chem. Soc., Perkin Trans. 1, 1994, 643 RSC.
  13. (a) F. H. Allen, S. A. Bellard and O. Kennard, Acta Crystallogr., Sect. C, 1986, 42, 829 CrossRef; (b) G. Bernardelli, C. W. JeVord, J. Boukouvalas, D. Jaggi and S. Kohmoto, Acta Crystallogr., Sect. C, 1987, 43, 701 CrossRef.
  14. E. L. Eliel and S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, pp. 766–767 Search PubMed.
  15. See J. Z. Gougoutas, in The Chemistry of Peroxides, ed. S. Patai, Wiley, New York, 1983, pp. 375–415 Search PubMed.
  16. SHELXS-86, G. M. Sheldrick, Acta Crystallogr., 1990, A46, 467 Search PubMed.
  17. SHELXTL/PC (Vers. 5.03), G. M. Sheldrick, University of Göttingen, 1994.
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