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 the following order: CH 2I 2 > CH 2Br 2 > CH 2Cl 2.
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