Abstract
Polymer supported carboxylic acids were cleaved quantitatively by boron triiodide, since the linker was attached to the substrate by an aryl alkyl ether bond. Various reagent to substrate ratios as well as ratios of the reagents (sodium tetrahydrido borate to iodine) were tested. Partial reduction also happened during the cleavage, due to the unreacted sodium tetrahydrido borate present in the reaction mixture and because the new NaBH 4/BX 3 system generated in the reaction mixture proved to be a very powerful reducing agent. Yields were compared to the similar cleavage reaction of ethers by hydriodic acid. Yields were the function of the initial concentration of boron triiodide. Structures of the cleaved substrates were evaluated by infrared and 1H NMR spectroscopy. The cleaved polymer could be reused with 26.7% loss of its original activity.
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