Abstract
Oxidation and reduction are two important transformations in organic chemistry. Although several oxidation and reduction reactions are studied in practical organic chemistry, Birch reduction as an experiment, is generally avoided. It is rather taught in theory sessions only. There are certain practical difficulties and hazards associated with these experiments. Benkeser reduction, however, is a safer variant of Birch reduction which can be performed by students under the supervision of a teacher. Foregoing text is a comparative account between Birch and Benkeser reductions. Additionally, it also provides an experimental procedure to prepare electride salt solutions which can be employed for a variety of reductions.
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Suggested Reading
Jie Jack Li, Name Reactions: A Collection of Detailed Reaction Mechanisms, 3rd expanded edn, Springer Berlin Heidelberg New York, pp.53–54, 2006.
Robert A. Benkeser, Robert E. Robinson, Dale M. Sauve, Owen H. Thomas, Reduction of Organic Compounds by Lithium in Low Molecular Weight Amines: Selective Reduction of Aromatic Hydrocarbons to Monoölefins, J. Am. Chem. Soc., Vol.77, No.12, pp.3230–3233, 1955.
E M Kaiser, R A Benkeser, Δ9−10-octalin, Organic Syntheses, Vol.50, pp.88–64, 1970.
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N R Dhatrak is working as Assistant Professor of Chemistry at the Department of Chemistry, Savitribai Phule Pune University, Pune. His research interests are total synthesis/design, and the development of laboratory instruments.
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Dhatrak, N.R. Birch and Benkeser Reductions. Reson 24, 735–740 (2019). https://doi.org/10.1007/s12045-019-0835-z
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DOI: https://doi.org/10.1007/s12045-019-0835-z