Metal-Ammonia Reduction of Aromatic Molecules

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Abstract
Metal-ammonia reduction is a highly efficient and convenient method of reduction of polycyclic as well as monocyclic aromatic hydrocarbons and their derivatives. With proper control over experimental conditions, reduction can generally be limited to a single stage; the structures of the primary products accord with theoretical predictions based on simple HMO calculations. Reduction in liquid ammonia and the related reductive alkylation reaction are reviewed from a preparative viewpoint with emphasis on the effects of structure, stereochemistry, and the selection of experimental techniques.

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