136887-32-6Relevant articles and documents
Deoxydative Substitution of Pyridine 1-Oxides by Thiols. Part XX. Reactions of (2, 3, and 4-Phenyl)-, 3-Acetamido-, 3-Bromo-, 3-Acetoxy-, 3-Ethoxypyridine 1-Oxides with 1-Adamantanethiol in Acetic Anhydride
Prachayasittikul, Sulpaluk,Doss, George,Bauer, Ludwig
, p. 1051 - 1060 (2007/10/02)
Substitutions of 2, 3, and 4-substituted pyridine 1-oxides by 1-adamantanethiol in acetic anhydride takes place at available α-, to a lesser degree at β-, and rarely at γ-ring carbons.It was found that 2-phenylpyridine 1-oxide produces a mixture of 5- and 6-(1-adamantylthio)-2-phenylpyridines, and 4-phenylpyridine 1-oxide a mixture of 2- and 3-isomeric sulfides.Substitutions of the 1-oxides of 3-phenyl-, 3-acetamido-, 3-acetoxy-, 3-bromo-, and 3-ethoxypyridine by 1-adamantanethiol in acetic anhydride led to mixtures consisting predominantly of 2- and 6-sulfide, and to a lesser extent, the 5-sulfide.When triethylamine is present in otherwise identical reaction mixtures, the ratio of α to β-sulfides increases.From the reactions of 3- and 4-phenylpyridine 1-oxides, there were isolated some N-acetyl hydroxy (or acetoxy) 1-adamantylthio substituted 1,2,3,4- and 1,2,3,6-tetrahydropyridines, whose structures are discussed.
