Amine oxides acylamines

The next step in the development of periodate oxidation was made by Nicolet and Shinn.8 They applied periodate oxidation to a series of a-amino acids, and found that those containing the 2-hydroxyamine structure are almost instantaneously oxidized. For such an oxidation to proceed rapidly, the amine could not be tertiary. An a-hydroxy A-acylamine was attacked very slowly, if at all. Only a small number of compounds were investigated. 

Conversion of an amine into a substituted amide is a convenient and widely used method for the protection of amino groups. Monoacylation of a primary amine often affords sufficient protection, i.e., against oxidation, alkylation, etc., and more complete protection is obtained by forming cyclic diacyl derivatives. Acyclic diacylamines easily revert to mono-acylamines and have only been used under very mild conditions [20]. Of the simple acylamines in common use the stability increases in the order formyl < acetyl < benzoyl and many more complex acyl groups have been evaluated in order to adjust the stability of the derivatives for various purposes. 

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