KINETICS AND MECHANISM OF THE ACID-CATALYSED BUTANOLYSIS OF 1,6-ANHYDRO-β-D-GLUCOPYRANOSE

Article abstract of DOI:10.1016/0008-6215(88)80014-4

The sulfuric acid-catalysed reaction of 1,6-anhydro-β-D-glucopyranose in 1-butanol at 80 deg C gave butyl α- and β-D-glucopyranoside as the sole products.The initial kinetic α/β ratio was 1.5, and the final α/β ratio upon equilibration was 2.7.The four pseudo-first-order reaction rate constants involved have been determined.Conformational studies showed that the reaction probably proceeds via a ¹C₄-B_o.3 interconversion of 1,6-anhydro-β-D-glucopyranose and a ⁴H₃-like oxycarbonium species.