Abstract
Nitrilium hexachloroantimonates 1a–c react with pyridine N-oxides 2a, d, f, j, m, o to afford bicyclic 2,3-dihydropyridinium salts 5a–p. The constitution of 5f was secured by an X-ray crystallographic analysis. Compounds 5 proved to be thermally labile (23–82°C) rearranging to 2-acylamino- pyridinium salts 6a, f–i or decomposing to tars. The benzimidazole-3-oxide 7 reacts with nitrilium salts 1a, b to 2-acylaminobenzimidazoles 9a, b. The experimental results as well as AM1 calculations support a mechanism for the reaction of nitrilium cations with heterocyclic nitrones, which has originally been suggested by Abramovitch [25, 26].
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