Abstract
The relative rates of chlorination of substituted benzaldehydes with CCl 3SO 2Cl (I) have been determined in dilute CCl 4 solution at 80° by means of competitive reactions using p-diethylbenzene as reference standard. A polar effect (ϱ = −0·54) correlated by the Hammett equation with the σ constant was found to differ from the value (−0·74) previously reported for BrCCl 3. Different selectivity values were obtained for I and BrCCl 3 toward benzaldehyde, ethylbenzene, benzyl methyl ether, benzhydryl methyl ether, and benzyl benzhydryl ether. These results indicate that the CCl 3SO 2 radical is mainly responsible for benzylic hydrogen-abstraction.
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