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Howarth, Michael (1962) Derivatives of substituted phenylboronic acids. Doctoral thesis, Northern Polytechnic.
The methods of obtaining arylboron dihalides have been critically surveyed and a new method of obtaining them viz. by the reaction of an arylmercuric halide with the corresponding boron trihalide has been investigated. By comparison of the infra-red spectra of the dichlorides with those of the dibromides it has been found possible to assign both the asymmetric and symmetric stretching modes and deformation modes of the B-Cl and B-Br bonds.
The various methods of obtaining the organomercury compounds themselves have been investigated and it has been found that the best ways are the reaction of a Grignard reagent with a mercuric halide, and the decomposition of an aryldiazonium mercury trichloride with copper powder.
A series of dialkyl p-bromophenylboronates have been prepared and characterised. Their infra-red spectra were also recorded and assignments of the vibration frequencies of the B-O, B-Phenyl, and O-O bonds made. The densities and refractive indices of the esters were measured and their observed molar refractivities compared with values calculated from the atomic refractivities of the constituent elements.
The arylboron dihalides were also used for the preparation of a new series of heterocyclic compound containing boron by reacting them with either catechol or 2,3-dihydroxynaphthalene. The ultraviolet spectra of these compounds were recorded and compared with the spectra of their parent compounds in an attempt to show the presence of aromatic stability.
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