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Title: Studies in the diphenyl series
Author: Bell, Frank
Awarding Body: University of Surrey
Current Institution: University of Surrey
Date of Award: 1926
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The result of the experimental work outlined below (1-4) appear to be in conflict with the stereochemical formula for diphenyl proposed by Kaufler. (1) 4-Hydroxylaminodiphenyl, 4-nitrosomethlaminodiphenyl, and 4-benzoylhydroxy-4 -acetylaminodiphenyl did not show the migration reactions characteristic if their benzene analogues. 4-Diacetylhydroxylaminodiphenyl was converted by hydrochloride acid into 3-chloro-4-aminodiphenyl. (2) Alkaloidal salts of 2-carboxydiphenyl, diphenic acid, and methyl hydrogen diphenate were crystallised without indication of resolution into optically active components. (3) The condensation products of benzidine with benzil, benzoin, and diacetyl were found not to be of simple character. (4) Tetramethylbenzidine when nitrated under varying conditions gave rise to position isomerised only. An alternative formula for diphenyl suggested by Turner (Nature, 1923, 112, 439) cannot be of wide application, since it has now been shown that the reactive hydrogen atom in both 4-dimethylaminodiphenyl and 4-hydroxydiphenyl is that in the 3-position. That antecedent substitution in the directing group is of considerable importance in determining the position taken by the entering radical follows from the results obtained in the nitration of 4-benzylideneaminodiphenyl, 4acetylaminodipjenyl, 4-p-toluenesulphonylaminodipenyl, and 4-p-toluenesulponylhydroxydiphenyl and in the bromination od 4-aminodiphenyl and 4-hydroxydiphenyl, and 4-methoxydipenyl is described in detail. Derivatives of 3:4-diaminodiphenyl are described, and a contribution made to the chemistry of the benztriazoles. A brief summary of the theoretical part is given on p. 35, whilst a summary of the experimental part (with a list of the 65 new compounds described) is given on p. 69.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available