Site-selectivity in the reaction of 3-substituted pyridine 1-oxide with phosphoryl chloride was investigated. When a strongly electron-withdrawing group (e.g. CN, CONRR', COOR, or NO2) was substituted at the 3-position, the reaction of 3-substituted pyridine 1-oxides with phosphoryl chloride yielded 3-substituted 2-chloropyridines as the main products.

3-Substituted Pyridine 1-Oxides with Strongly Electron-Withdrawing Groups Produce 3-Substituted 2-Chloropyridines when Reacted with Phosphoryl Chloride

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Site-Selectivity in the Reaction of 3-Substituted Pyridine 1-Oxides with Phosphoryl Chloride

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