CGC, MS AND THEORETICAL-STUDIES ON THE TRANSFORMATION MECHANISM OF O-ACETYL-1,5-ANHYDRO-2-DEOXY-D-THREO-PENT-1-ENITOL IN AQUEOUS-SOLUTIONS

Heating O-acetyl-1,5-anhydro-2-deoxy-D-threo-pent-1-enitol (per-O-acet yl-D-xylal) in water leads to a mixture of unsaturated compounds with cyclic, as well as open-chain structures. The mixture obtained was ana lysed by CGC and CGC-MS methods. The experimental findings were employ ed to model the mechanism of the transformation studied. In addition, the AM1 calculations were carried out in order to describe the element ary processes suggested. Full geometry optimizations performed for spe cies found in the mixture made it possible to evaluate the thermodynam ic characteristics of particular reactions. Next, the calculations for transition states afforded appropriate kinetic barriers. All computat ions were carried out for the gaseous phase as well as in aqueous solu tion. Both experimental and theoretical results are in good accordance with the mechanism proposed.