TRIDENTATE COMPLEXES OF PERIODATE AND SOME FURANOSE DERIVATIVES,
Abstract
1,2-O-Isopropylidene-alpha-D-glucofuranose (I) is highly resistant to glycol scission by periodate in alkaline solution. This atypical effect is caused by preferential formation of a stable periodate complex. Proton magnetic resonance spectroscopy shows that the 3-, 5-, and 6-protons of I (and the 3- and 5-protons of I-6,6'-d2) become strongly deshielded during this process, which, together with accompanying changes in proton-proton coupling, establishes that the complex (II) has a 3,5,6tridentate structure. Variations in the stability of II with pH suggest that it can exist either as a monoanion or dianion. A complex analogous to II is formed by ethyl alpha-D-thioglucofuranoside, whereas methyl beta-Dgalactofuranoside forms a complex that probably has the 2,5,6-structure. The characteristics of these tridentate complexing reactions support the general concept that a five-membered cyclic complex is a transient intermediate of a-glycol oxidation by periodate. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Mar 04, 1965
- Accession Number
- AD0618806
Entities
People
- A. S. Perlin
- E. Von Rudloff
Organizations
- National Research Council Canada