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Photochemical Interaction between Ketones and Secondary Alcohols

Nature volume 141, pages 1012–1013 (1938)Cite this article

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

Authors
  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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