华东师范大学学报(自然科学版) ›› 2010, Vol. 2010 ›› Issue (4): 125-130.

• 化学化工 • 上一篇    下一篇

羰基化合物与二卤海因的α-卤代反应

陈梓湛， 管细霞， 郑祖彪， 邹新琢   

  1. 华东师范大学 化学系，上海 200062
  • 收稿日期:2009-09-01 修回日期:2010-01-01 出版日期:2010-07-25 发布日期:2010-07-25
  • 通讯作者: 邹新琢

α-Halogenation of carbonyl compounds with 1,3-dihalo-5,5-dimethylhydantoin

CHEN Zi-zhan， GUAN Xi-xia， ZHENG Zu-biao， ZOU Xin-zhuo   

  1. Department of Chemistry, East China Normal University, Shanghai 200062, China
  • Received:2009-09-01 Revised:2010-01-01 Online:2010-07-25 Published:2010-07-25
  • Contact: ZOU Xin-zhuo

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摘要： 报道了脂肪（环）酮与1,3-二溴-5,5-二甲基海因（DBDMH）在甲醇中、室温下进行的α-溴代反应，并在此基础上，进一步报道了以脂肪（环）酮、β酮酯和丙二酸酯为底物，使用1,3-二氯-5,5-二甲基海因（DCDMH）和对甲苯磺酸在乙腈中、室温下进行的α-氯代反应.其中β-酮酯和丙二酸酯以87%~96%的高收率得到α-单氯代反应产物.

关键词: α-氯代, α-溴代, 脂肪酮, β-酮酯, 丙二酸酯, 3-二溴-5, 3-二氯-5, α-氯代, α-溴代, 脂肪酮, β-酮酯, 丙二酸酯, 3-二溴-5, 3-二氯-5

Abstract: α-Bromination of aliphatic ketones using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) in methanol at room temperature was described. α-Chlorination of aliphatic ketones, β-keto-esters and malonic ester using 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) and p-toluenesulfonic acid in acetonitrile at 25 ℃ was also reported. β-Keto-esters and dimethyl malonate give α-monochloroproducts in high yields (87%~96%).

Key words: α-bromination, aliphatic ketones, β-keto-esters and malonic ester, 3-dichloro-5, 5- dimethylhydantoin, α-chlorination, α-bromination, aliphatic ketones, β-keto-esters and malonic ester, 3-dichloro-5, 5- dimethylhydantoin

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