A short review of cases where acyl- or alkoxycarbonyl onium salts have been prepared or postulated as intermediates is presented.
The reaction of trialkylamines with chloroformate esters and
acyl halides has been re-examined. Chloride ion proved to be too
nucleophilic an anion to be able to isolate the salts. The route
of decomposition is discussed in detail. The reaction of amines with
chloroformates in the presence of antimony pentachloride has been
investigated. Chloride ion exchange using triethyloxonium tetrafluoroborate
has been achieved in the reaction of phenyl chloroformate
with triethylamine, and the 13C nmr spectrum of this salt is discussed
in detail. [Continues.]
A Doctoral Thesis. Submitted in partial fulfillment of the requirements for the award of Doctor of Philosophy of Loughborough University.