Abstract
Abstract The new 2-aryl-2-iminio dithioacetates 1 are easily available by reaction of acetophenones with different sulfurdioxide-secondary amine complexes and sulfur. A short summary of the syntheses and reactions of related zwitterionic compounds 2–5 is given. The 2-iminium dithioester salts 6 have been prepared by reaction of 1 with several alkylating agents. The hydrolysis of 6 is a new route to 2-oxo dithioesters 7. Because the iminium function in 6 is of higher reactivity in reaction with amines than the dithioester group the novel 2-imino dithioesters 10 and 2,2-diamino dithioesters 12 could be synthesized by reaction of 6 with primary and secondary amines, respectively. 5a was converted into the cyclic monothiooxamide 17 by application of the synthetic strategy to the compounds of the diaminocarbenium dithiocarboxylate type 4 and 5. X-ray structure determinations of 6a, 10f and 12b are presented as examples of these new classes of dithioesters.
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