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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 11
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Original Articles

Double Hunsdiecker Reactions. Convenient Preparation of 1,1-Dibromocyclopropane and 1,1-Dibromocyclobutane

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Pages 983-987 | Published online: 06 Dec 2006

References

  • Doering , W. v. E. and Hoffmann , A. K. 1954 . J. Am. Chem. Soc. , 76 : 6162
  • Seyferth , D. , Burlitch , J. M. , Minasz , R. J. , Mui , J. Y.-P. , Simmons , H. D. Jr. , Trieber , A. J. H. and Dowd , S. R. 1965 . J. Am. Chem. Soc. , 87 : 4269
  • Barnier , J-P. , Rousseau , G. and Conia , J.-M. Synthesis , 1983 915
  • Brinker , U. H. and Schenker , G. J. Chem. Soc., Chem. Commun. , 1982 769
  • Seetz , J. W. F. L. , Akkerman , O. S. and Bickelhaupt , F. Tetrahedron Lett. , 1981 4855 Double Hunsdiecker degradation of cyclopropane-1,2-dicar-boxylic acid has been reported
  • David , J. A. , Hernyk , J. , Carroll , S. , Bunds , J. and Johnson , D. 1965 . J. Org. Chem. , 30 : 415
  • Singh , R. K. and Danishefsky , S. 1975 . J. Org. Chem. , 40 : 2969 Org. Synth., 1981, 60, 66
  • Cristol , S. J. and Firth , W. C. 1961 . J. Org. Chem. , 26 : 280
  • Through use of refluxing dichloromethane as the solvent, reaction was usually complete within 3 h. Comparable handling in carbon tetrachloride at 70°C required in excess of 15 h for discharge of the bromine color
  • Abell , P. I. and Tren , R. 1965 . J. Org. Chem. , 30 : 4212

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