Abstract
IN order to draw general conclusions as to the mechanism of reduction by dissolving metals from the data obtained in the course of a number of reductions by sodium and alcohol in liquid ammonia1,2,3, it is necessary to determine more precisely the role of the solvent. That its use is not essential for the hydrogenation of benzene derivatives to a-dihydro-compounds is shown by the fact that anisole, dimethylaniline or m-aolyl methyl ether when treated in boiling light petroleum (b.p. 100 120°) with potassium and the equivalent amount of ethyl, or better, isopropyl alcohol, gave the dihydro-derivatives already obtained1,3. This was shown by conversion to the 2:4-dinitrophenylhydrazone of α3-cyclohexenone, m.p. 133–134°, convertible by acid to the derivative of α2-cyclohexenone, m.p. 167°, and in the last case by preparation of the 2:4-dinitrophenylhydrazone of 3-methyl-β2-cyclohexenone, m.p. 174°3. The method has little practical value because of the small yields, except perhaps with compounds insoluble in ammonia; but it demonstrates that the solvent does not affect the nature of the products.
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References
Birch, J. Chem. Soc., 430 (1944).
Birch, J. Chem. Soc., 809 (1945).
Birch, J. Chem. Soc., 593 (1946).
Levy and Cope, J. Amer. Chem. Soc., 66, 1684 (1944). Birch, unpublished work.
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BIRCH, A. Reduction by Dissolving Metals. Nature 158, 585 (1946). https://doi.org/10.1038/158585c0
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DOI: https://doi.org/10.1038/158585c0
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