Chemistry of pyridine. VI. Steric and electronic effects influencing the deoxidative substitution of pyridine N-oxide by mercaptans in acetic anhydride was written by Hershenson, Fred M.;Bauer, Ludwig. And the article was included in Journal of Organic Chemistry in 1969.Formula: C7H9NO This article mentions the following:
The deoxidative substitution of 1-oxide derived from pyridine, 2-, 3-, and 4-picoline, 4-tert-butylpyridine, 4-phenylpyridine, and 2,6-, 3,4-, and 3,5-lutidine by tert-BuSH in Ac2O is reported. Ring substitution introduced a tert-BuS group at any one of the available α positions (2,6-lutidine 1-oxide being the exception) and only at those β positions which had originally free α positions adjacent to them. Mechanisms to explain both α and β substitution via 1-acetoxy-2-tert-butylthio-1,2-dihydropyridines are postulated. Evidence is presented that β substitution involves migration of the sulfide function from such 1,2-dihydropyridines via episulfonium intermediates. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Formula: C7H9NO).
3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Formula: C7H9NO