THE SOLVOLYSIS OF THE ALPHA- AND BETA-3,4,6-TRI-O-ACETYL-D-GLUCOPYRANOSYL CHLORIDES
- 1 January 1955
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 33 (1) , 128-133
- https://doi.org/10.1139/v55-016
Abstract
3,4,6-Tri-O-acetyl-β-D-glucopyranosyl chloride was found to undergo solvolysis in acetic acid to form 1,3,4,6-tetra-O-acetyl-α-D-glucopyranose as the main reaction product. The much less reactive anomeric α-chloride also appeared to undergo solvolysis with extensive inversion of the anomeric center. It is submitted that the tendencies for inversion obtained in these ionic reactions are due to the conformations imposed on the intermediate ions through distribution of the positive charge to the ring oxygen and the consequent introduction of double-bond character to the carbon-1 to ring-oxygen bond.Keywords
This publication has 7 references indexed in Scilit:
- The Role of Neighboring Groups in Replacement Reactions. XX. Some Conversions of Cyclopentane and Indan Derivatives1Journal of the American Chemical Society, 1953
- Stereochemistry of the Cholesterol Dibromides1Journal of the American Chemical Society, 1950
- Mechanisms for the formation of acetylglycosides and orthoesters from acetylglycosyl halidesJournal of Research of the National Bureau of Standards, 1949
- The Role of Neighboring Groups in Replacement Reactions. XII. Rates of Acetolysis of 2-Substituted Cyclohexyl Benzenesulfonates1Journal of the American Chemical Society, 1948
- The Thermodynamic Properties and Molecular Structure of Cyclohexane, Methylcyclohexane, Ethylcyclohexane and the Seven Dimethylcyclohexanes1Journal of the American Chemical Society, 1947
- The Structure of Molecules Containing Cyclohexane or Pyranose Rings.Acta Chemica Scandinavica, 1947
- The Effect of Mercuric Bromide on the Hydrolysis of Acetobromoglucose in Acetone.Acta Chemica Scandinavica, 1947