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在铁粉存在下,以商用N,N-二甲基甲酰胺(DMF)作溶剂,90℃、氮气保护下,二芳基二硒醚与α-溴代羰基化合物反应,得到一系列α-芳硒基羰基化合物.考察了温度、时间、溶剂及铁粉用量对反应的影响,其中,温度对反应的影响最为明显.α-溴代羰基化合物中羰基上取代基对反应有很大影响,取代基为苯基时,转化率较甲基或烷氧基时低.反应机理可能是铁插入Se—Se键中形成亲核性Se Fe Se,随后与亲电底物α-溴代羰基化合物发生亲核取代.本方法使用铁粉促进断裂Se—Se键具有原料安全无毒、廉价易得、实验操作简便等优点.
In the presence of iron powder, commercial N, N-dimethylformamide (DMF) as solvent, under the protection of nitrogen at 90 ℃, the diaryldiselenide and α-bromocarbonyl compound were reacted to obtain a series of α- The effects of temperature, time, solvent and the amount of iron powder on the reaction were investigated. Among them, the influence of temperature on the reaction was the most obvious. Substituents of the carbonyl group in α-bromocarbonyl compound greatly influenced the reaction, When the substituent is phenyl, the conversion rate is lower than that of methyl or alkoxy. The reaction mechanism may be that iron is inserted into the Se-Se bond to form a nucleophilic Se Fe Se, followed by reaction with the electrophilic substrate α-bromocarbonyl compound Nucleophilic substitution occurs. The method uses iron powder to promote fracture Se-Se bond has the advantages of safe and non-toxic raw materials, cheap and easy to operate, experimental operation is simple and so on.