Affiliations: Institut für Anorganische Chemie der Georg-August-Universität Göottingen,Tammannstrasse 4, D-37077 Göottingen, Germany | Institute of Organic Chemistry NAS of Ukraine, Murmanskaya str. 5, 02660, Kiev, Ukraine
Abstract: 1,3-Dialkyl-4,5-dimethylimidazole-2-thiones 1a, 1b and acyclic N,N,N’,N’-tetramethylthiourea 3 react with sulfuryl dichloride to yield a new type of sulfur ylides, 1,3-dialkyl-4,5-dimethylimidazol-2-ylidenesulfonium dichloromethylides 2a, 2b and bis(dimethylamino)-methylenesulfonium dichloromethylide 4, respectively. The reaction of 2a and 4 with acetylacetone results in the formation of thione S-ylides 5 and 6, whereas the reaction with dimethyl(trimethylsilyl)amine leads to the formation of S-dimethylaminothiouronium chlorides 8a, 8b, and 9, respectively. Anion metathesis of 8a, 8b, and 9 with NaX affords compounds 10a – 10c, 11a, and 11b (X = BPh4, BF4). Compounds 8a and 9 are involved in a [3 + 2] cycloaddition reaction when treated with dimethyl acetylenedicarboxylate, resulting in salt-like derivatives of isothiazolines 12 – 15. These new compounds have been characterized by spectrometric and elemental analyses, and the solid-state structure of compound 10a has also been determined by single-crystal X-ray structural analysis.
