Phenylgermane, benzylgermane and p-tolylgermane were obtained by reduction of the corresponding organotrichlorgermanes prepared by organomercuration reactions of germanium tetrachloride. Phenylgermane was also prepared by the reaction of germyl bromide with phenyllithium, and p-digermylbenzene, with p-bromogermylbenzene, by reaction of germyl bromide with the exchange products from the reaction of n-butyllithium and p-dibromobenzene. The effectiveness of the reagent sodium germyl (and potassium germyl) was investigated in reactions with methylene chloride and bromide for the preparation of digermylmethane, which was also made by reduction of bis(trichlorogermyl)methane prepared from cesium trichlorogermanate(II). The usefulness of the halogenation of germane by carbon tetrachloride and tetrabromide, and methyl and hydrogen bromide, for the preparation of germyl chloride and bromide was investigated. Vibrational assignments were made to characteristic bands in the infrared spectra of the new aromatic germanium hydrides and some chloro derivatives. Ion fragmentation patterns were examined. The proton nuclear magnetic resonance spectra of the organogermanium hydrides and chloro derivatives were interpreted on the basis of the existence of germanium-aromatic ring (p → d) π bonding, but this effect was not very important for the interpretation of the ultraviolet spectra. Calculation of the energy levels of toluene, phenylsilane and phenylgermane by the Extended Hückel method and comparison with ultraviolet spectral data indicated that (p → d) π bonding was important only in phenylsilane. / French abstract, if available fr

Thesis (Ph.D.)--McGill University. / Typewritten MS.

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