Glycol cleavage overoxidation

Oxidations Other Than Glycol Cleavage Overoxidation 189... 

In theory, periodate oxidation could have given a clear-cut answer as to the composition of the isomeric mixture of deoxy ribose phosphates. The 4-phosphate (73), devoid of vicinal diol groups, should be resistant to periodate the 3-phosphate (74) should reduce one and only one molar equivalent of the oxidant and yield one molar equivalent of both formaldehyde and the phosphorylated dialdehyde (75), whereas the 5-phosphate (76) could be expected to reduce one molar equivalent of periodate relatively rapidly, followed by a slower overoxidation reaction owing to the oxidation of malonaldehyde, formed as a result of the glycol cleavage. 

Products formed in the overoxidation of such compounds with lead tetraacetate have not been so well characterized, although acetoxylation might be ex-pected to occur. Some compounds examined as models of these activated methine groups, or as possible products of glycol cleavage— for instance,... 

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