Preliminary Studies On The Chlorination Of Alcohols Using Imidoyl Chloride Catalized By Sulfoxides

We reported a mild and efficient procedure for converting alcohols into the corresponding halides in this paper. The chlorination reagent was N-phenylbenzimidoylchloride and the catalyst was DMSO. Anhydrous chloroform was used as solvent. The reaction conditions were optimized according to different alcohols. When the substrates were benzyl alcohols and allyl alcohols, the reaction went smoothly at room temperature; when the substrates were secondary alcohols, the reaction was carried out at reflux temperature. The reaction is high-yielding (70～91%) and the reaction time short (0.5～1.5 h), the reaction conditions mild (20～65℃). To understand the mechanism of the reaction, we used optical active alcohols as starting materials. Configuration invertions were observed in the chlorination. Further, respective addition of KI, NaN3 and tetrabutylammoniun bromide to the chlorination in order to prove the reaction mechanism. The structures of the products were fully characterized by IR, 1HNMR, GC and GC-MS.A possible mechanism for the reaction was proposed and further experiments need to be carried out.