KINETICS AND MECHANISM OF THE ACID-CATALYZED REACTIONS OF METHYLATED TRIOSES

Article abstract of DOI:10.1016/S0008-6215(00)85190-3

In aqueous hydrochloric acid, 2,3-di-O-methyl-D-glyceraldehyde and 1,3-dimethoxy-2-propanone undergo acid-catalyzed reactions producing 2-oxopropanal.The kinetics of these two reactions were studied polarographically.The kinetic data obtained and the incorporation of deuterium from the medium into the 2-oxopropanal formed (isolated as 2-methylquinoxaline and analyzed mass spectrometrically), allowed formulation of a mechanism for the acid-catalyzed reaction of both methylated trioses.The mechanism proposed are in agreement with quantum-chemical calculations of the charge distribution in the compounds studied and in some of their important intermediates.