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Lappert, M. F. (1951) Interaction of boron trichloride with alcohols and ethers. Doctoral thesis, Northern Polytechnic.
The sequences of reactions which occur in the following systems have been investigated.
(1) Boron trichloride - Alcohol
(2) Boron trichloride - Tri-alkyl borate
(3) Hydrogen Halide - Tri-alkyl borate
(4) Boron trichloride - Ether
In system (1) the influence of (a) structure, (b) relative proportions of reagents, (c) temperature has been studied with special reference to the formation and stability ranges of alkyl dichloroboronites, ROBCl₂, and di-alkyl chloroboronates, (RO)₂BCl, the alcohols examined being the following:
n-propyl, isopropyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl and n-octyl alcohols. 1-Phenylethanol and octan-2-ol were used in an optically active condition in order to secure further evidence of mechanism.
The influence of pyridine was studied, and there emerged a convenient general method for the preparation of tri-alkyl borates. In system (2) the ease and consequences of proportionation and disproportionation were special features. Dealkylation studies in system (3) afforded evidence of mechanism in system (1), and observations in these three systems contribute to explanations of data obtained in system (4).
Experimental data are correlated and explained in terms of fundamental modes of approach ot reacting molecules and in terms ot accepted concepts designated SN2, SN1, SNi. Correlations with other non-metallic inorganic halide - alcohol systems (e.g. PCl₃ - ROH) are also considered.
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