Preparation of α-substituted acroleins via the reaction of aldehyde or the corresponding ozonide with dihalomethane and diethylamine

被引:43
作者
Hon, YS [1 ]
Chang, FJ [1 ]
Lu, L [1 ]
Lin, WC [1 ]
机构
[1] Natl Chung Cheng Univ, Dept Chem, Chiayi 621, Taiwan
关键词
D O I
10.1016/S0040-4020(98)00216-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of aldehydes or the corresponding ozonides with a mixture of dibromomethane and diethylamine afforded alpha-substituted acroleins in modest to good yields. The beta-carbon of the acrolein (nc, n = 1-16) derived from dibromomethane. Functional groups, such as ketone, hydroxy, acetoxy, bromide, iodide, ester are compatible with this reaction condition. The relative rates and yields of this transformation in dichloromethane were found to be in the following order: CH2I2 > CH2Br2 > CH2Cl2. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5233 / 5246
页数:14
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