Letter | Published:

Photochemical Interaction between Ketones and Secondary Alcohols

Nature volume 141, pages 10121013 (04 June 1938) | Download Citation

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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. 1.

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

  2. 2.

    , and , Z. physikal. Chem., B, 5, 124 (1929); 12, 165, 194 (1931).

  3. 3.

    and , J. Chem. Physics., 1, 362 (1933). Compare also Bergmann and Schuchardt, Liebig's Ann., 487, 225 (1931).

  4. 4.

    , Z. physikal. Chem., B, 12, 151 (1931). and , J. Amer. Chem. Soc., 59, 2450, 2453 (1937).

  5. 5.

    and , Ber. dtsch. Chem. Ges., 70, 376 (1937).

  6. 6.

    For the formula of this compound see Lettré and Inhoffen, "Sterine, Gallensaeuren, etc.", p. 135 (Stuttgart, 1935); , 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.

  7. 7.

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

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Affiliations

  1. Daniel Sieff Research Institute, Rehovoth, Palestine. April 3.

    • CH. WEIZMANN
    • , Y. HIRSHBERG
    •  & E. BERGMANN

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https://doi.org/10.1038/1411012a0

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