E. Dart, G. Holt
Oct 1, 1974
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0
Influential Citations
2
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
Acylation rather than sulphonylation is the major primary reaction when the isomeric chlorosulphonylbenzoyl chlorides (I) are stirred with aluminium chloride (1 or 2 mol. equiv.) and benzene at room temperature. The ortho-isomer (I) also yielded o-benzoylbenzenesulphinic acid (V) and chlorobenzene by reduction of the first-formed o-benzoylbenzenesulphonyl chloride. When ethylene dichloride is used as solvent, sulphonylation is almost completely inhibited and there is no reduction of the ortho-isomer. This provides a convenient synthesis for o-, p-, and the previously unknown m-benzoylbenzenesulphonyl chlorides. Electron-attracting groups in the nucleus of benzenesulphonyl chloride retard sulphonylation whereas the same substituents in benzoyl chloride accelerate acylation.