1310826-06-2Relevant academic research and scientific papers
Synthesis of new imidazole 3-oxides; unexpected deoxygenation of some derivatives in the reaction with 2,2,4,4-tetramethylcyclobutane-1,3-dithione
Mloston, Grzegorz,Jasinski, Marcin,Rygielska, Dorota,Heimgartner, Heinz
experimental part, p. 765 - 776 (2011/05/12)
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 electronwithdrawing 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.
