10.1002/(SICI)1522-2675(19980909)81:9<1585::AID-HLCA1585>3.0.CO;2-N
The research investigates the reaction of azole N-oxides with thioketones to produce imidazole-2(3H)-thiones and other products. The purpose is to explore the potential of azole N-oxides in sulfur-transfer reactions, which could provide new synthetic routes for heterocyclic compounds. Key chemicals used include 1,4,5-trisubstituted imidazole 3-oxides, cyclobutanethiones, and various thioketones like thiobenzophenone and thioketene. The study concludes that azole N-oxides efficiently undergo sulfur-transfer reactions with thioketones, yielding imidazole-2(3H)-thiones in high yields. The mechanism involves a nucleophilic attack by the N-oxide's oxygen on the thioketone's C-S bond, forming a zwitterionic intermediate that leads to the final products. This reaction pathway is supported by experimental observations and provides a useful method for synthesizing imidazole-2(3H)-thiones without isolating intermediate compounds.
10.1021/jo00342a036
The research focused on the synthesis and investigation of a new class of reactive organosulfur compounds known as α-chlorothiosulfenyl chlorides (R2C(Cl)SSCl), which were derived from the reaction of various aromatic and aliphatic thiones with sulfur dichloride in dry carbon disulfide. The study aimed to explore the potential of these compounds and understand the mechanisms involved in their transformations. The researchers found that the reaction of α-chlorothiosulfenyl chlorides with triphenylphosphine regenerates the thiones, accompanied by the corresponding ketones. Key chemicals used in the process included sulfur dichloride, carbon disulfide, thiones such as thiobenzophenone, xanthione, and various other aromatic and aliphatic thiones, as well as triphenylphosphine. The conclusions drawn from the research highlighted the formation of α-chlorothiosulfenyl chlorides and their potential synthetic utility, noting their unusual reactivity with multiple electrophilic sites and the complexity of the products formed upon reaction with triphenylphosphine.
