Abstract
THE reduction of the keto group in tropinone (I) to the secondary alcoholic stage gives the two internally compensated stereoisomerides tropine and ψ-tropine (II). The nature of the reduction product depends on the reducing agent used. When the reduction is done electrolytically or with zinc and hydriodic acid, tropine is the main product1. However, the reduction product is always contaminated with small amounts of ψ-tropine. With sodium amalgam tropinone is reduced to ψ-tropine only1. As the formation of tropine and ψ-tropine from tropinone involves the reduction of a ketone to a secondary alcohol, it could be foreseen that lithium aluminium hydride would be a specific reagent for it2. However, the interest lay in knowing the exact nature of the reduction product (or products) obtained.
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References
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MIRZA, R. Reduction of Tropinone with Lithium Aluminium Hydride. Nature 170, 630 (1952). https://doi.org/10.1038/170630a0
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DOI: https://doi.org/10.1038/170630a0
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