THE TRANSFORMATION MECHANISM OF -ACETYL-1,5-ANHYDRO-2-DEOXY-D-ARABINO-HEX-1-ENITOL IN WATER

Heating of -acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (per-O-a cetyl-D-glucal) in water leads to a mixture of unsaturated compounds w ith cyclic as well as open-chain structures. The mixture obtained was analyzed by the CGC method. The experimental findings were employed to model the mechanism of the transformation studied. In addition, AM1 c alculations were carried out in order to describe the elementary proce sses suggested. Full geometry optimizations performed for species foun d in the mixture made it possible to evaluate the thermodynamic charac teristics of particular reactions. Next, the calculations for transiti on states afforded appropriate kinetic barriers. All computations were carried out for a gaseous phase as well as an aqueous solution. Both experimental and theoretical results conform well with the mechanism p roposed.