Reaction of sodium aluminum hydride with selected organic compounds containing representative functional groups. Comparison of the reducing characteristics of lithium and sodium aluminum hydrides

The approximate rate and stoichiometry of the reaction of excess sodiumaluminum hydride (SAH) with organic compounds containing representative functional groups under standardized conditions (tetrahydrofuran, 0 o C) were examined in order to define the reducing characteristics of the reagent and compare the reducing power with lithium aluminum hydride (LAH). In general, the reducing action and power of the reagent are similar to those of LAH. All of the active hydrogen compounds including alcohols, amines, and thiols evolve hydrogen instantly. Aldehydes and ketones are reduced very rapidly and quantitatively to give the corresponding alcohols