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Influence of the polymer on an anionic activation reaction promoted by a supported crown ether

Authors
Journal
Polymer
0032-3861
Publisher
Elsevier
Publication Date
Volume
25
Issue
8
Identifiers
DOI: 10.1016/0032-3861(84)90352-5
Keywords
  • Polymer Supported Reagent
  • Polymer Supported Crown Ether
  • Crown Ether
  • Polymer Effect
  • Anionic Activation
  • Koenigs-Knorr Reaction

Abstract

Abstract The reaction of alcohols with tetra- o-acetylbromoglucose in the presence of silver nitrate (Koenigs-Knorr reaction) is re-examined. The influence of several crown ethers, cryptands and supported ligands are studied. With t-BuOH, the reaction leads to a mixture of sugar nitrate and glycoside. We discuss the yield and the selectivity obtained with free and immobilized ligands. Supported macrocycles which assist the reaction increase the glycoside formation. The polymer effect on the selectivity is explained in terms of steric hindrance.

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