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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 8, 1978 - Issue 1
33
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Original Articles

A Ring Cyclized Product from the Delepine Reaction

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Pages 45-51 | Received 17 Oct 1977, Published online: 06 Dec 2006

References

  • Angyal , S. J. 1953 . Organic Reactions , 8 : 197
  • Grethe , G. , Lee , H. L. , Uskoković , M. and Brossi , A. 1968 . J. Org. Chem. , 33 : 494
  • Grethe , G. , Lee , H. L. , Uskovović , M. and Brossi , A. 1968 . J. Org. Chem. , 33 : 491
  • Harcourt , D. N. and Waigh , R. D. 1971 . J. Chem. Soc. C , : 967
  • No advantageous precipitation occurred with chloroform as solvent and a complex mixture (exclusive of starting material by t.l.c.) was formed
  • The ratio of the yields of (I) and (II) was not altered appreciably when the hydrogen chloride concentration was varied in the range 0.1–5M. Hydrolysis using 2M‐aqueous hydrochloric acid led to enhancement of the proportion [ca 3:1 by 1H‐n.m.r. spectral analysis of the acetyl region of the derived acetamides (III) and (IV)] of the non‐cyclized product (1)
  • A full discussion of the spectral assignments will be presented elsewhere
  • Torchia , D. A. , Lyerla , J. R. Jr. and Deber , C. M. 1974 . J. Amer. Chem. Soc. , 96 : 5011
  • Campbell , R. , Haworth , R. D. and Perkin , W. H. Jr. 1926 . J. Chem. Soc. , : 32 Earlier attempts to effect ring closure of 3′,4′‐dimethoxyphenacylamine with aqueous formaldehyde were also not successful

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