Cu(OAc)₂·H₂O/Biimidazoles, Iodobenzene Diacetate Promoted Reactions Of Sulphoxide With 1, 3-dicarbonyl Compounds

Iodobenzene diacetate is widely applied in the organic reactions. It plays the role as oxidant and substrate respectively. This paper is divided into two parts.For the first part, we stressed reactions of sulphoxide with 1,3-dicarbonyl compounds promoted by Cu(OAc)2·H2O, 2,2′-biimidazole and iodobenzene diacetate. We studied reactions of sulphoxide with aliphatic and aromatic 1,3-dicarbonyl compounds promoted by Cu(OAc)2·H2O, 2,2′-biimidazole and iodobenzene diacetate, with the presence of K2CO3 as a base and DMSO a solvent. Through experiments we found that: most aliphatic 1,3-dicarbonyl compounds can react with DMSO and give sulfoxoniumylid compounds. Thus we discovered a new type of reaction promoted by iodobenzene diacetate. But the aromatic 1,3-dicarbonyl compounds made a difference with the unexpected acetoxylated compounds present. In addition, we also studied other sulfoxide compounds, but no expected products were found.In the second part, synthesis of disulfides by iodobenzene diacetate was investigated. N-phenyl thiocarbamates were oxidized by iodobenzene diacetate and gave the corresponding disulfides compounds. This reaction can proceeds easily in short time with a high yield even at a room temperature.The structures of products were confirmed by 1H NMR, 13C NMR and HRMS spectra. Based on these reactions, we proposed mechanisms for iodobenzene diacetate -promoted reactions to achieve a further application in our organic chemistry.