Accession Number : AD0618806

Title :   TRIDENTATE COMPLEXES OF PERIODATE AND SOME FURANOSE DERIVATIVES,

Corporate Author : NATIONAL RESEARCH COUNCIL OF CANADA SASKATOON (SASKATCHEWAN) PRAIRIE REGIONAL LAB

Personal Author(s) : Perlin,A. S. ; von Rudloff,E.

Report Date : 04 MAR 1965

Pagination or Media Count : 7

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)

Descriptors :   (*GLYCOSIDES, COMPLEX COMPOUNDS), (*CARBOHYDRATES, COMPLEX COMPOUNDS), (*IODATES, COMPLEX COMPOUNDS), (*COMPLEX COMPOUNDS, CARBOHYDRATES), GLYCOLS, OXIDATION, DECOMPOSITION, STABILIZATION, NUCLEAR MAGNETIC RESONANCE, IONS, MONOCYCLIC COMPOUNDS, CANADA

Distribution Statement : APPROVED FOR PUBLIC RELEASE