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Photochemical Interaction between Ketones and Secondary Alcohols

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Abstract

IT has been observed by various authors1 and recently confirmed by an extensive investigation in our laboratory, that under the influence of ultraviolet light, secondary alcohols and ketones undergo a process of mutual oxidation and reduction. This can consist of a complete hydrogen exchange, or of the formation of pinacols,

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References

  1. See e.g. Ciamician and Silber, Ber. dtsch. Chem. Ges., 36, 1575 (1903) and later.

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  6. For the formula of this compound see Lettré and Inhoffen, "Sterine, Gallensaeuren, etc.", p. 135 (Stuttgart, 1935); Inhoffen, Naturwiss., 25, 125 (1937). This ergopinacol seems to be formed from ergosterol through a series of hydrogen migrations; otherwise it would be inconceivable that a hydrogen atom at C7 should leave the molecule.

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  7. The analogous reaction is given by dehydro-ergosterol dehydro-lumisterol and dehydro-cholesterol. Windaus and Linsert, Annalen, 465, 148 (1928), Dimroth, Ber. dtsch. Chem. Ges., 69, 1123 (1936); Urushibara, Chem. Centralblatt, 1, 2982 (1937).

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Authors and Affiliations

  1. Daniel Sieff Research Institute, Rehovoth, Palestine

    CH. WEIZMANN, Y. HIRSHBERG & E. BERGMANN

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  1. CH. WEIZMANN
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  2. Y. HIRSHBERG
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  3. E. BERGMANN
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WEIZMANN, C., HIRSHBERG, Y. & BERGMANN, E. Photochemical Interaction between Ketones and Secondary Alcohols. Nature 141, 1012–1013 (1938). https://doi.org/10.1038/1411012a0

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