Formation mechanism of 2,6-dimethyl-2,6-octadienes from thermal decomposition of linalyl β-D-glucopyranoside

Abstract

Thermally decomposed products of (±)-linalyl β-D-glucoside were analyzed by GC and GC/MS. 2,6-Dimethyl-2,6-octadienes produced by mild pyrolysis of linalyl β-D-glucopyranoside under a vacuum were detected and characterized by MS and NMR spectroscopy. This suggests that 2,6-dimethyl-2,6-octadienes are produced during thermal decomposition of the glucoside via proton transfer from the anomeric position to C-6 in the aglycon moiety. A stable isotope labeling experiment directly indicated the new reaction mechanism.