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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 9
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Original Articles

Alumina-promoted Opening of Medium Ring Epoxides: cis-Cyclooctene Oxide - trans-2-Acetoxycyclooctanol

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Pages 737-741 | Published online: 06 Dec 2006

References

  • Department of Physical Sciences, Kingsborough Community College of CUNY, Brooklyn, NY 11235
  • Parker , R. E. and Isaacs , N. S. 1959 . Chem. Rev. , 59 : 737
  • Buchanan , J. B. and Sable , H. Z. 1972 . “ Selective Organic Transformation ” . In Stereoselective Epoxide Cleavages Edited by: Thyagarajan , B. S. Vol. 2 , New York : Wiley Interscience . in;
  • Rosowsky , A. 1964 . Heterocyclic Compounds with Three- and Four-Membered Rings, Part I Edited by: Weissberger , A. 1 – 523 . New York, NY : Interscience Publishers .
  • Posner , G. H. and Rogers , D. Z. 1977 . J. Amer. Chem. Soc. , 99 : 8208 – 8214 .
  • Posner , G. H. , Rogers , D. Z. and Romero , A. 1979 . Israel J. Chem. , 18 : 259
  • Posner , G. H. and Hulce , M. 1980 . J. Catal. , 64 : 497
  • Posner , G. H. 1978 . Angew. Chem. Int. Ed. Engl. , 17 : 487
  • McKillop , A. and Young , D. W. 1979 . Synthesis see also, 401
  • Cope , A. C. , Moon , S. and Peterson , P. E. 1959 . J. Amer. Chem. Soc. , 81 : 1650
  • Cope , A. C. , Grisar , J. M. and Peterson , P. E. 1959 . ibid. , 81 : 1640
  • Cope , A. C. , Keough , A. H. , Peterson , P. E. , Simmons , H. E. and Wood , G. W. 1959 . ibid. , 79 : 3900
  • Brockmann , H. and Schodder , H. 1971 . Chem. Ber. , 74B : 73 W-200-N alumina is purchased in 500 g or 1,000 g metal containers from ICN Pharmaceuticals Inc., Cleveland, Ohio (or from Woelm Pharma, Eschwege, W. Germany). This alumina is reported to have activity “super-I” on the Brockmann scale [.] and to have a surface area of 200 m2/g. It is used as received. Comparable yields have been obtained with W-200-N alumina from the same can which has been used and then stored in a nitrogen-filled glove bag for several months. Woelm alumina is the best source of alumina we have found for this procedure. Using less than 10g of Al2O3, per mmol of oxide in this procedure is not satisfactory
  • Diethyl ether (Baker) is used as received. The diethyl ether is poured rapidly into the reaction vessel;syringe techniques are not required. Dry carbon tetrachloride also has been used successfully in place of diethyl ether
  • Acetic acid (Allied Chemical and Dye Corp) is distilled before use, bp760-118[ddot], and is stored over 4Å molecular sieves

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