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1,3-Dipolar character of six-membered aromatic rings. Part XVI. Reactions of benzyne with 3-hydroxypyridine, 1-methyl-3-oxidopyridinium, and related compounds
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1976
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Successive CycloadditionsDerivative (Chemistry)HeterocyclicBiochemistrySix-membered Aromatic RingsNatural SciencesMolecular BiologyOrganic Chemistry6-Methyl AnalogueChemistryRelated CompoundsBenzyne Cycloadduct FormationPharmacologyHeterocycle ChemistryChemical DerivativeSynthetic Chemistry1,3-Dipolar Character
3-Hydroxypyridine, its 6-methyl analogue, and 4-hydroxyisoquinoline all react with 2 mol. equiv. of benzyne cycloadduct formation occurs across the 2- and 6-positions together with N-phenylation. 1-Methyl-3-oxidopyridinium and its 6-methyl analogue both react with 2 mol. equiv. of benzyne in two successive cycloadditions.