Author Topic: Periodic Acid Oxidation of Vicinal Diols.  (Read 830 times)

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cattleprodder

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Periodic Acid Oxidation of Vicinal Diols.
« on: September 08, 2003, 12:31:00 PM »
Vicinal diols (>CHOH-CHOH<) can be made from alkenes by using either osmium tetraoxide (OsO4) or slightly basic, cold, aqueous KMnO4. 

From there, the vicinal diol can be oxidized with periodic acid (HIO4) to form two new aldehydes.  The net result is the same products which would be obtained by using ozonolysis. 

Provided that the potassium permanganate could be kept from forming substituted benzoic acids, elemicin and myristicin could in this way be transformed into mescaline and lophophine after reductively aminating the aldehyde with ammonium acetate, MeOH and sodium cyanoborohydride.

"Periodic Acid Oxidation"
from _Organic Reactions_, Vol. 2, 1944, pp. 362-363, by Ernest L. Jackson.

"Oxidation of Alginic Acid:  15g (0.085 equivalent) of dried alginic acid is stirred vigorously with 425cc of 0.380M periodic acid solution until peptized, which requires about one and one half hours.  The mixture is kept at room temperature for 20 to 24 hours, during which time the periodic acid is reduced (1.1 mole per equivalent of alginic acid).  The oxidation proceeds comparatively rapidly during the first two hours.  Addition of 1600cc of t-butyl alcohol throws down an amorphous precipitate.  This is centrifuged down and washed 4x with 50cc portions of aqueous t-butyl alcohol (1 part alcohol to 3 parts water).  After being dried at 30mm. over sulfuric acid, the resulting fluffy white residue weighs 13 grams."

The book gives other examples as well.

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