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Synthesis 1970; 1970(4): 161-172
DOI: 10.1055/s-1970-21589
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Metal-Ammonia Reduction of Aromatic Molecules

Ronald G. HARVEY*
  • *Ben May Laboratory, University of Chicago, Chicago, Illinois 60637
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Publication History

Publication Date:
12 September 2002 (online)

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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.