Abstract
INSPECTION of the literature reveals that hydrogenation of many, but not all, cyclic allylic alcohols gives products in which at least one hydrogen has been added to the same side of the molecule as the hydroxyl group. Thus, Schoenheimer and Evans1 reported that hydrogenation of allocholesterol (I) in amyl ether solution in the presence of a platinum catalyst gave coprostanol (in unstated yield). A re-investigation of this reaction was undertaken in an attempt to determine more precisely the influence of hydroxyl or other neighbouring groups on the stereochemistry of hydrogen addition.
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References
Schoenheimer, R., and Evans, E. A., J. Biol. Chem., 114, 567 (1936).
Adams, R., and Shriner, R. L., J. Amer. Chem. Soc., 45, 2171 (1923).
Keenan, C. W., Giesemann, B. W., and Smith, H. A., J. Amer. Chem. Soc., 76, 229 (1954).
Wicker, R. J., J. Chem. Soc., 2165 (1956).
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DART, M., HENBEST, H. Effect of Alkali Salts on the Steric Course of Hydrogenation of a Cyclic Allylic Alcohol. Nature 183, 817–818 (1959). https://doi.org/10.1038/183817a0
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DOI: https://doi.org/10.1038/183817a0
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