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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 6
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Original Articles

Beckmann Fission of Some Fused Cyclobutanones: A New Entry into Indole-2-Acetonitriles and Benzo[b]thiophene-2-acetonitrile

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Pages 437-449 | Published online: 05 Dec 2006

References

  • Ali , S. M. , Lee , T. V. and Roberts , S. M. 1977 . Synthesis , : 155 For examples, see; J. M. Conia and M. J. Robson, Angew. Chem. Int. Ed., 14, 473 (1975); R. D. Miller and D. R. McKean, Tetrahedron Letters, 1003 (1979)
  • Donaruma , L. G. and Heldt , W. Z. 1960 . Org. Reac. , 11 : 2 This is the first application of Beckmann fission to cyclobutanone oximes. For Beckmann fission, see
  • Ikeda , M. , Matsugashita , S. and Tamura , Y. 1976 . J.C.S. Perkin I , : 2587
  • Schindler , W. 1957 . Helv. Chim. Acta , 40 : 2156
  • Blicke , F. F. and Sheets , D. G. 1949 . J. Am. Chem. Soc. , 71 : 2856
  • Jurian , D. R. and Foster , R. 1973 . J. C. S. Chem. Commun. , : 312 As yet no details have been reported for their experiments
  • The alcohols 3a were separated by column chromatography into endo- and exo-3a. The stereochemistry was assigned on the basis of the fact that sodium borohydride reduction of 4a gave exclusively the endo-3a.
  • The alcohols 8 were separated by chromatography into endo- and exo-8. The stereochemical assignment was based on the fact that sodium borohydride reduction of 9 gave exclusively the endo-8.
  • Illi , V. O. 1979 . Synthesis , : 387

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