Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl
The relative rates of chlorination of substituted benzaldehydes with CCl3SO2Cl (I) have been determined in dilute CCl4 solution at 80° by means of competitive reactions using p-diethylbenzene as reference standard. A polar effect (ρ{variant} = -0·54) correlated by the Hammett equation with the σ con...
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| Format: | Article |
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Elsevier
1970
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| Online Access: | http://eprints.um.edu.my/24697/ https://doi.org/10.1016/S0040-4020(01)92979-5 |
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| Summary: | The relative rates of chlorination of substituted benzaldehydes with CCl3SO2Cl (I) have been determined in dilute CCl4 solution at 80° by means of competitive reactions using p-diethylbenzene as reference standard. A polar effect (ρ{variant} = -0·54) correlated by the Hammett equation with the σ constant was found to differ from the value (-0·74) previously reported for BrCCl3. Different selectivity values were obtained for I and BrCCl3 toward benzaldehyde, ethylbenzene, benzyl methyl ether, benzhydryl methyl ether, and benzyl benzhydryl ether. These results indicate that the CCl3SO2 radical is mainly responsible for benzylic hydrogen-abstraction. © 1970. |
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