ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Reactions of saccharides catalyzed by molybdate ions. XV. Mechanism of the epimerization reaction

V. Bílik, L. Petruš, and V. Farkaš

Institute of Chemistry, Slovak Academy of Sciences, 809 33 Bratislava

Abstract:  Epimerization reaction catalyzed by molybdate ions was studied with D -glucose- 1-³H and D-mannose-2-³H. A possible mechanism of the epimerization reaction is discussed, where the change of configuration involves mutual exchange of hydrogen atoms in the positions C-1 and C-2. The hydrogen transfer is mediated by a transitient state with formation of tricentric bond between the carbon atoms C-1 and C-2 of the aldose.

Full paper in Portable Document Format: 295a690.pdf

Chemical Papers 29 (5) 690–696 (1975)