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

YS Hon, FJ Chang, L Lu, WC Lin

Index: Hon, Yung-Son; Chang, Feng-Jon; Lu, Ling; Lin, Wei-Chi Tetrahedron, 1998 , vol. 54, # 20 p. 5233 - 5246

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Citation Number: 37

Abstract

Treatment of aldehydes or the corresponding ozonides with a mixture of dibromomethane and diethylamine afforded α-substituted acroleins in modest to good yields. The β-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 ...