Heteroaromatic N-oxide rearrangements. Reinvestigation of 1,3 tosyloxy migration in the reaction of isoquinoline N-oxide with tosyl chloride
Isoquinoline N-oxide (2) reacts with 18O-enriched tosyl chloride to furnish 18O-labeled 4-tosyloxy-isoquinoline (4), which was assessed for oxygen isotopic enrichment by NMR and mass spectrometry. The 30-45% 18O incorporation at the bridging oxygen is inconsistent with a high level of the intramolecular tight-ion-pair ('sliding') mechanism. A combination of two intramolecular mechanisms is probably operative.
Maryanoff,Zhang,Reitz,Leo,Jones
p. 7247 - 7250
(2007/10/02)
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