Alumina-promoted Opening of Medium Ring Epoxides: cis -Cyclooctene Oxide - trans -2-Acetoxycyclooctanol
- 1 January 1981
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 11 (9) , 737-741
- https://doi.org/10.1080/00397918108063651
Abstract
Opening of epoxides is usually achieved homogeneously by treating oxiranes with strong acids or strong bases; several reviews of this subject are available.2 We have discovered that commercially available chromatographic -alumina promotes highly efficient heterogeneous opening of a wide range of epoxides by a variety of nucleophiles (e.g., alcohols, acetic acid, amines, mercaptans, and selenols) under extraordinarily mild (25[ddot]) and neutral conditions and that this procedure is the method of choice for clean nucleophilic opening of medium ring epoxides.3Keywords
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