2-Propanone, 1,3-dihydroxy-, oxidation

The scope of the reaction was considerably enlarged in 1935, when Clutterbuck and Reuter6 observed that the compound tetrahydroterrein, derived from the mold metabolite terrein, consumes more than the calculated amount of periodate per mole. They found that 1,2-diketones and a-hydroxy ketones are also oxidized under the conditions used by Malaprade. Although this type of oxidation had been earlier noted [in a study7 of the action of periodate on 1,3-dihydroxy-2-propanone (dihydroxyace-tone)], Clutterbuck and Reuter made a more thorough exploration of the reaction.6 In a series of model compounds, Ri and R2 were varied from... 

The glyceritol phosphate (VI) has the 1-0-phospho-D (that is, 3-0-phos-pho-L) configuration since it is oxidized by Codehydrogenase I ( diphospho-pyridine nucleotide ) in the presence of glycerophosphate dehydrogenase (specific toward L-3-glycerophosphate ) to 1,3-dihydroxy-2-propanone phosphate. 

This Scheme is the most probable, but requires verification, because, by preparative electro-oxidation of the product of condensation of o-phenylenediamine with l,3-dihydroxy-2-propanone, 2-benzimidazole-methanol was obtained in only a low yield. The equilibrium con-... 

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