Non-Malapradian oxidation

A problem frequently encountered is overoxidation or non-Malapradian oxidation. Most examples of this kind of behavior involve the formation, as a product of the cleavage reaction, of tartronaldehyde and related compounds containing an active hydrogen atom. Glycuronic adds and some other carboxylic derivatives are subject to extensive overoxidation attributable to instability of the product of normal scission— for instance, 11, or to dehydrogenation at C-5. Similarly, substituted tartronaldehydes (12), which are formed during oxidation of... 

S. R. Sarfati and P. Szabo, Quantitative determination with periodate of compounds subject to non-Malapradian oxidation. Part III. Cyclohexanehexols, Carbohydr. Res., 11 (1969) 571-573. S. J. Angyal, D. Greeves, and V. A. Pickles, The stereochemistry of complex formation of polyols with borate and periodate anions, and with metal cations, Carbohydr. Res., 35 (1974) 165-173. 

Cantley, M., L. Hough, and A. O. Pittet The non-malapradian oxidation of carbohydrates and related compounds by periodate. J. Chem. Soc., 1963, 2527-... 

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