The mutarotation, hydrolysis, and rearrangement reactions of D-glucosylamine, D-mannosylamine, and D-xylosylamine have been studied, and rationalized on the basis of the formation of an intermediate, acyclic imonium ion. Rate constants are given for the hydrolysis reaction under various conditions. The formation of diglycosylamines is explained as a type of transamination in which a second molecule of the glycosylamine reacts with the first (in the imonium ion form) with the subsequent elimination of ammonia. Unsubstituted D-glucosylamine has been found to undergo an Amadori rearrangement in glacial acetic acid or in some of the methylenic compounds found by Hodge and Rist to be effective in the rearrangement of N-substituted glyeosylamines. Intramolecular mechanisms are suggested to account for the effectiveness of carboxylic

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