Reaction Of Pyridine N-oxides Research Articles

The mechanisms of the reactions of p-toluenesulfonyl chloride with isoquinoline- and pyridine n-oxides

The mechanisms of the reactions of isoquinoline- and pyridine N-oxides have been studied using oxygen-18 as a tracer. p-Toluenesulfonyl chloride labeled with 18O was reacted with isoquinoline N-oxide, yielding 4-tosyloxyisoquinoline, a portion of which was further hydrolyzed yielding 4-hydroxyisoquinoline. The analytical results suggest that the main path of this reaction proceeds via “intimate ion pair” as depicted by VI. In the reaction of pyridine N-oxide with p-toluenesulfonyl chloride, 18O tracer study suggests that a similar rearrangement via “intimate ion pair” as VI takes place with the formation of 3-tosyloxypyridine.