Facile oxidation of benzyl ethers by the 2-nitrobenzenesulfonylperoxyl intermediate generated from 2-nitrobenzenesulfonyl chloride and superoxide

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Yong Hae Kim, Yong Il Kim and Joong Young Kim


Abstract

Various benzyl ethers react with a 2-nitrobenzenesulfonylperoxyl radical intermediate generated from 2-nitrobenzenesulfonyl chloride and potassium superoxide at –25 °C in acetonitrile to give the corresponding esters in high yields.


References

  1. C. A. Godfrey, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Flemming, Pergamon, Oxford, 1991, vol. 7, p. 235 Search PubMed.
  2. P. F. Schuda, B. M. Cichowicz and M. R. Heimann, Tetrahedron Lett., 1983, 24, 3829 CrossRef CAS.
  3. B. S. Bal, K. S. Kochhar and H. W. Pinnick, J. Org. Chem., 1981, 46, 1492 CrossRef CAS.
  4. H.-J. Schmidt and H. J. Schafer, Angew Chem., Int. Ed. Engl., 1979, 18, 69 Search PubMed.
  5. E. C. Juenge and D. A. Beal, Tetrahedron Lett., 1968, 5819 CrossRef CAS.
  6. P. Angibeaud, J. Defaye, A. Gadelle and J.-P. Utille, Synthesis, 1985, 1123 CrossRef CAS.
  7. M. Sasidharan, S. Suresh and A. Sudalai, Tetrahedron Lett., 1995, 36, 9071 CrossRef CAS.
  8. M. Ochiai, T. Ito, H. Takahashi, A. Nakanishi, M. Toyonari, T. Sueda, S. Goto and M. Shiro, J. Am. Chem. Soc., 1996, 118, 7716 CrossRef CAS.
  9. Y. H. Kim and B. C. Chung, J. Org. Chem., 1983, 48, 1562 CrossRef; Y. H. Kim, B. C. Chung and H. S. Chang, Tetrahedron Lett., 1985, 26, 1079 CrossRef CAS; Y. H. Kim, H. K. Lee and H. S. Chang, Tetrahedron Lett., 1987, 28, 4285 CrossRef CAS; Y. H. Kim, K. S. Kim and H. K. Lee, Tetrahedron Lett., 1989, 30, 6357 CrossRef CAS.
  10. G. A. Russel and R. C. Williamson, J. Am. Chem. Soc., 1964, 86, 2357 CrossRef; R. L. Huang, H. H. Lee and S. H. Song, J. Chem. Soc., 1962, 3336 RSC.
  11. Y. H. Kim, S. C. Lim, M. Hoshino, Y. Ohtsuka and T. Ohishi, Chem. Lett., 1989, 167 CAS.
  12. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1991, ch. 2 Search PubMed.
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