由聚合物负载的N-硒基吗啉试剂合成α-卤代醛  

Synthesis of α-Haloaldehydes from Polymer-Supported (N-phenylseleno)morpholine

作　　者：徐曲[1] 周丽云[1] 刘晓玲[1] 宋才生[1] 

机构地区：[1]江西师范大学化学学院,江西南昌330027

出　　处：《江西师范大学学报（自然科学版）》2003年第3期265-268,共4页Journal of Jiangxi Normal University(Natural Science Edition)

基　　金：江西省自然科学基金资助课题(001109)

摘　　要：常温下,聚苯乙烯负载硒溴试剂和吗啉在二氯甲烷中反应得到新型的聚苯乙烯负载N-硒基吗啉试剂;聚苯乙烯负载N-硒基吗啉是含α-氢的醛有效的α-硒基化试剂,该负载型的α-硒基醛经卤代脱硒,以良好的产率(70%～92%)生成α-卤代醛,操作简便(过滤、洗涤),粗产物不需进一步提纯即具有好的纯度(>95%),N-硒基吗啉树脂可再生使用.两种新型的负载型N-硒基吗啉和α-硒基醛试剂无毒无味、使用方便,长时间保存其活性无明显下降.A novel polystyrene-supported (N-phenylseleno)morpholine was preparaed from polystyrene-supported selenium bromide and morpholine in CH2Cl2 at room temperature. Polystyrene-supported (N-phenylseleno)morpholine was an efficient α-selenenylating agent for saturated aldehydes bearing an α-hydrogen, and the α-haloaldehydes were prepared in good to moderate yields (70%～92%) and high purities (>95%) without further purification by halogenation-deselenenylation reaction from the corresponding α-selenoaldehyde resins on solid-phase.This method is more convenient and faster than the corresponding solution-phase method. Furthermore, the polystyrene-supported (N-phenylseleno)morpholine can be regenerated conveniently for recycling. A remarkable advantage of these new polymer-supported selenium reagents is the convenience of handling and their totally odorless nature as compared to the non-polymer-bound reagents. These polymer-supported selenium reagents are quite stable under the reaction conditions and can be stored in the air at room temperature for long time without loss of reactivity.

关 键 词：α-卤代醛 聚苯乙烯 N-硒基吗啉试剂 α-硒基醛试剂 固相有机合成 

分 类 号：O623.55[理学—有机化学] O621.3[理学—化学]