Novel synthesis of 10-membered cyclic bis-ethers from 4-(N-alkylanilino)but-2-yn-1-ols[hair space] 1

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Krishna C. Majumdar, Gour H. Jana and Udayan Das


Abstract

A number of symmetrical 10-membered cyclic bis-ethers 5a–f are synthesized in a single step in good yields from the reaction of 4-(N-alkylanilino)but-2-yn-1-ols 3a–f with m-chloroperbenzoic acid in dichloromethane at room temperature during 8 h.


References

  1. For a preliminary communication, see K. C. Majumdar, G. H. Jana and U. Das, Chem. Commun., 1996, 517 Search PubMed.
  2. (a) J. E. Baldwin, R. E. Hackler and D. P. Kelly, J. Chem. Soc., Chem. Commun., 1968, 538 RSC; (b) R. W. Jemison and W. D. Ollis, J. Chem. Soc., Chem. Commun., 1969, 294 RSC; (c) J. E. Baldwin, J. E. Brown and G. Hofle, J. Am. Chem. Soc., 1971, 93, 788 CrossRef CAS; (d) J. E. Baldwin, A. K. Bhatnagar and R. W. Harper, J. Chem. Soc., Chem. Commun., 1970, 659 RSC.
  3. Y. Makisumi and S. Natzumoto, Tetrahedron Lett., 1966, 6393 CrossRef; H. J. Hansen, B. Sutter and H. Schmid, Helv. Chim. Acta, 1968, 51, 828 CAS; V. Rautenstrauch, J. Chem. Soc., Chem. Commun., 1970, 4 RSC.
  4. H. E. Zimmermann, in Molecular Rearrangements, Part 1, ed. P. de Mayo, Interscience, New York, 1963, p. 345 Search PubMed.
  5. J. Meisenheimer, H. Greeske and A. Willmersdorf, Ber. Dtsch. Chem. Ges., 1922, 55, 513; R. F. Kleinschmidt and A. C. Cope, J. Am. Chem. Soc., 1944, 66, 1929 CrossRef CAS.
  6. R. B. Woodward and R. Hoffman, Angew. Chem., Int. Ed. Engl., 1969, 8, 781 CrossRef CAS.
  7. Y. Yamamoto, J. Oda and Y. Inouye, J. Chem. Soc., Chem. Commun., 1973, 848 RSC.
  8. E. P. Linton, J. Am. Chem. Soc., 1940, 62, 1945 CrossRef CAS.
  9. B. S. Thyagarajan, J. B. Hillard, K. V. Reddy and K. C. Majumdar, Tetrahedron Lett., 1974, 1999 CrossRef CAS; J. B. Hillard, K. V. Reddy, K. C. Majumdar and B. S. Thyagarajan, J. Heterocycl. Chem., 1974, 11, 369 CrossRef CAS; B. S. Thyagarajan and K. C. Majumdar, J. Heterocycl. Chem., 1975, 12, 43 CAS.
  10. K. C. Majumdar and S. K. Chattopadhyay, J. Chem. Soc., Chem. Commun., 1987, 524 RSC; K. C. Majumdar, S. K. Chattopadhyay and A. T. Khan, J. Chem. Soc., Perkin Trans. 1, 1989, 1285 RSC; K. C. Majumdar and S. K. Ghosh, J. Chem. Soc., Perkin Trans. 1, 1994, 2889 RSC.
  11. A. C. Cope and P. H. Towel, J. Am. Chem. Soc., 1949, 71, 3423 CrossRef CAS.
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