The Bilik reaction

The introduction of the Bilik reaction, the molybdic acid catalyzed interco nversion of epimeric aldoses, is an important milestone in carbohydrate che mistry. The essentials of this unique, stereospecific carbon-skeleton rearr angement of epialdoses are presented. Emphasis is laid on the latest develo pments in the area, namely the mutual interconversion of 2-ketoses and 2-C- (hydroxymethyl)aldoses, a reaction that is exploited for the preparation of some important representatives of these reducing sugars. Mechanistic studi es with isotopically substituted D-fructoses are also described.