ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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].
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19963380149
