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Paper | Regular issue | Vol 83, No. 4, 2011, pp.765-776
Published online, 1st March, 2011
DOI: 10.3987/COM-10-12130
Synthesis of New Imidazole 3-Oxides; Unexpected Deoxygenation of Some Derivatives in the Reaction with 2,2,4,4-Tetramethylcyclobutane-1,3-dithione

Grzegorz Mlostoń,* Marcin Jasinski, Dorota Rygielska, and Heinz Heimgartner*

*Department of Organic and Applied Chemistry, University of Łódź, Maritpwocza 68, PL-90-136 Łódź, Poland


Whereas the reaction of a series of 1,4,5-trisubstituted imidazole 3-oxides with 2,2,4,4-tetramethylcyclobutane-1,3-dithione gave the corresponding imidazole-2-thiones by a sulfur-transfer reaction via [2+3] cycloaddition, an unexpected deoxygenation occurred in the case of 4-acetyl-1-(adamantan-1-yl)-5-methylimidazole 3-oxide. It was shown that the presence of an electron- withdrawing substituent at C(4) and the bulky 1-adamantyl group at N(1) are necessary to enable this reaction course. A reaction mechanism via a zwitterion, followed by a 1,3-cyclization and elimination of an oxathiirane, is proposed.