Theoretical insight into the pyrolytic deformylation of levoglucosenone and isolevoglucosenone

Abstract

A computational study was conducted to gain insight into the pyrolytic deformylations of levoglucose-none and isolevoglucosenone. Present B3LYP/6-31G* and CBS QB3 calculations provide valuable evidence to rule out the formation of isolevoglucosenone during the pyrolytic degradation of cellulosic materials. This, along with the supplementary data herein presented and with other recent reports, suggest that levoglucosenone should not be formed directly from levoglucosan (as proposed in numerous reports), but rather from another intermediate, such as 1,4:3,6-dianhydro-a- D -glucopyranose.