Adamantylazoles:IX.Aeid-catalyzed Adamantylation of l,2,4-Triazol-3-thione

摘要

l,2,4-Triazole-3-thione reacts with 1-adamantanol in sulfuric acid to form l-(l-adamantyl)-3-[(l-adamantyl)sulfanyl]-l,2,4-triazole and 3,3'-disulfandiylbis[l-(l-adamantyl)-l,2,4-triazole].Alkylation of l,2,4-triazole-5-thione,like 1,2,4-tri-azol-5-ones and their derivatives,has best been studied in neutral or alkaline media.Triazolethiones are primarily alkylated by the sulfur atom to form(alkylsylfanyl)triazoles.N-Alkylation is observed in reactions involving formaldehyde,as well as on cyanoethylation of 2-phenyl-l,2,4-triazole-3-thione.Data on acid-catalyzed alkylation of l,2,4-triazole-3-thiones are lacking.