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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.3