Accession Number:

AD0618806

Title:

TRIDENTATE COMPLEXES OF PERIODATE AND SOME FURANOSE DERIVATIVES,

Descriptive Note:

Corporate Author:

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

Personal Author(s):

Report Date:

1965-03-04

Pagination or Media Count:

7.0

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

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Distribution Statement:

APPROVED FOR PUBLIC RELEASE