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Wheelans, M. A. (1956) Interaction of boron trichloride with carboxylic acids and their esters. Doctoral thesis, Northern Polytechnic.
An historical review of the interaction of selected non-metallic galides and alcohols, carboxylic acids and their esters is given, together with a detailed account of work connected with systems involving acyl boron compounds.
An account of the interaction of boron trichloride and acetic acid and chloro-substituted acetic acids describes the stoicheiometry of these systems. As a result of this work and a reinvestigation of previous work in boric acid - acetic acid systems it is believed that a useful contribution is made towards solving the controversy about the nature of acyl boron compounds.
A study of the interaction of boron trichloride and esters of carboxylic acids (RCO2R'), in which the groups R and R' are varied affords a number of interesting results. Where R is the trichloroacetyl group no interaction occurs but where R and R' are simple aliphatic groups addition compounds are formed and these decompose with ester fission accompanied, in the case of esters of acids such as benzoic and chloro-substituted acetic acids, by dissociation. Except where R' is a secondary or tertiary alkyl group, alkyl dichloroboronites are formed: RCO2R', BC13 → RCOCl + R'OBCl2.
Secondary and tertiary alkyl acetates give a different result, the boron remaining with the acyl group as dichloro-diacetyl diborate:
3RCO2R' 2BCl3 = CH3COO-B-O-B-OCOCH3 3RCl CH3COCl. Cl Cl
This compound is also prepared by interaction of boron trichloride and acetic acid and its anhydride. Alcoholysis and pyrolysis of this and other acyl boron compounds are studied.
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