Journal of East China Normal University(Natural Sc ›› 2010, Vol. 2010 ›› Issue (4): 125-130.

• Article • Previous Articles     Next Articles

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

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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