S. Ōae, K. Ikura
Jun 1, 1967
Citations
0
Influential Citations
9
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
When 4-nitropyridine N-oxide was allowed to react with p-nitrobenzenesulfenyl chloride, 4-pyridyl 4′-chloropyridinium chloride (V) and 4-(4′-pyridol)pyridine (IV) were obtained, along with p, p-dinitrodiphenyl disulfide, p-nitrobenzenesulfonic acid, and a salt, presumed to have a VI structure. Similar products were formed in the reaction between 4-chloropyridine N-oxide with p-nitrobenzenesulfenyl chloride. In the case of 4-methoxypyridine N-oxide, however, a simple reduction was the main reaction; thus 4-methoxypyridine was obtained, while the other products were the same. As in the case of pyridine- and α-picoline N-oxide, no ring-substituted product was isolated in the reactions of these N-oxides. Apparently, the reaction of these N-oxides with p-nitrobenzenesulfenyl chloride involves the initial formation of the salt, which has a N-sulfenoxy bond, (Remark: Graphics omitted.), which presumably cleaves homolytically in the succeeding step to give the final products.