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Chem."],"accepted":{"date-parts":[[2019,2,8]]},"abstract":"<jats:p>Adamantyloxyamine reacts with formaldehyde to give <jats:italic>N<\/jats:italic>-(adamantyloxy)formaldimine as a room-temperature-stable compound that exists in solution in monomeric form. This product was used for reactions with \u03b1-hydroxyiminoketones leading to a new class of 2-unsubstituted imidazole 3-oxides bearing the adamantyloxy substituent at N(1). Their reactions with 2,2,4,4-tetramethylcyclobutane-1,3-dithione or with acetic acid anhydride occurred analogously to those of 1-alkylimidazole 3-oxides to give imidazol-2-thiones and imidazol-2-ones, respectively. Treatment of 1-(adamantyloxy)imidazole 3-oxides with Raney-Ni afforded the corresponding imidazole derivatives without cleavage of the N(1)\u2013O bond. Finally, the <jats:italic>O<\/jats:italic>-alkylation reactions of the new imidazole <jats:italic>N<\/jats:italic>-oxides with 1-bromopentane or 1-bromododecane open access to diversely substituted, non-symmetric 1,3-dialkoxyimidazolium salts. Adamantyloxyamine reacts with glyoxal and formaldehyde in the presence of hydrobromic acid yielding symmetric 1,3-di(adamantyloxy)-1<jats:italic>H<\/jats:italic>-imidazolium bromide in good yield. Deprotonation of the latter with triethylamine in the presence of elemental sulfur allows the in situ generation of the corresponding imidazol-2-ylidene, which traps elemental sulfur yielding a 1,3-dihydro-2<jats:italic>H<\/jats:italic>-imidazole-2-thione as the final product.<\/jats:p>","DOI":"10.3762\/bjoc.15.43","type":"journal-article","created":{"date-parts":[[2019,2,19]],"date-time":"2019-02-19T11:57:00Z","timestamp":1550577420000},"page":"497-505","source":"Crossref","is-referenced-by-count":13,"title":["Synthesis and selected transformations of 2-unsubstituted 1-(adamantyloxy)imidazole 3-oxides: straightforward access to non-symmetric 1,3-dialkoxyimidazolium 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