Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl

Kheng H. Lee

Document Type

Article

Publication Date

1-1-1970

Abstract

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.

Keywords

Polar effects, hydrogen abstraction, benzaldehydes-II, radical chlorination

Divisions

CHEMISTRY

Publication Title

Tetrahedron

Volume

26

Issue

5

Publisher

Elsevier

Additional Information

Lee, K.H.; Department of Chemistry, University of Malaya, Malaysia

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