Summary
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1.
It was shown for the first time that sodium borohydride has a reducing action on alkyl halides (polyhalomethanes), and selectivity of the reduction was observed.
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2.
Carbon tetrabromide was converted into bromoform (yield 74%) and iodoform into methylene iodide (yield 85%); a subsequent stage of reduction in both cases was not observed under the experimental conditions.
Literature cited
N. D. Gaylord, Reduction with Complex Metal Hydrides (Interscience Publishers, London-N. Y., 1956), p. 911.
V. Dibeler, J. of Research 44, 363 (1950).
K. A. Kocheshkov, J. Russ. Chem. Soc. 60, 1191 (1928); Compare Organic Syntheses, Vol. I [Russian translation] (For. Lit. Press, 1949), p. 123.
V. Auger, O. r. 145, 810 (1907); 146, 1282 (1908); compare organic Syntheses, Vol. I [Russian translation) (For. Lit. Press, 1949), p. 222.
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Nad, M.M., Kocheshkov, K.A. Selective reduction of polyhalomethanes by means of sodium borohydride. Russ Chem Bull 6, 1144–1145 (1957). https://doi.org/10.1007/BF01169395
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DOI: https://doi.org/10.1007/BF01169395