Acyltrialkylammonium salts

Tertiary aliphatic amines cannot be acylated by the chlorides of simple carboxylic acids. When reaction occurs, the chlorides lose hydrogen halide, affording ketenes588 which readily undergo further reaction in individual cases of, / -unsaturated acyl chlorides, acyltrialkylammonium salts can be... 

Acylation of tertiary aliphatic amines to acyltrialkylammonium salts by means of acyl chlorides has recently been achieved by Klages,614 by adding antimony pentachloride to the reaction mixture so that the actual acylating agent is an acylium hexachloroantimonate ... 

These acyltrialkylammonium salts are stronger acylating agents than acyl chlorides themselves. 

Acyltrialkylammonium salts have been prepared and were found to be very active in the alkylation of benzyl cyanide. These quats are more resistant to Hoffmann degradation than simple tetralkylammonium salts, which allows the reaction to be run at higher temperatures [46]. 

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