Chloracylierung und Bromacylierung von Carbonylverbindungen. IV. Bildungsmechanismus von Carbonsäure‐(1‐halogenalkyl)estern

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Abstract
Chloroacylation and bromoacylation of carbonyl compounds IV. Investigations of the reaction mechanismThe kinetics of the Lewis acid catalyzed reaction between acyl chlorides and carbonyl compounds (especially aldehydes) is investigated by 1H‐NMR.‐spectroscopy. With acetyl chloride as starting material a second order reaction is observed; the rate of the reaction increases in polar solvents as well as with increasing electron‐donating capacity of the aldehyde. ‐ With benzoyl chloride as starting material the reaction is first order with respect to benzoyl chloride, but zero order with respect to the aldehyde. The reaction rate is strongly influenced by the substituents of the benzoyl chloride. ‐ Two polar reaction mechanisms which are in accord with these results are outlined and discussed.