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Title: The configuration of 22-bridged diphenyls
Author: Bird, Gwendoline Ruth
Awarding Body: University of London
Current Institution: Royal Holloway, University of London
Date of Award: 1953
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The thesis is divided into five sections. 1. A review is given of some of the aspects of the stereochemistry of diphenyl and its derivatives, 2. The attempt has been made to resolve a diphenyl derivative in which the 2 and 2' positions in diphenyl are linked by a 7-membered ring and the 6 and 6' positions are free from substituents. Such a compound should be capable of existing in enantiomorphic forms as it possesses no element of symmetry. Ho optically active compound has been isolated, but in one case two diastereoisomeric quinine salts of widely different rotation were obtained which yielded an inactive acid on decomposition. The idea is put forward that non-resolution of such compounds is due to the difference in specific rotation of the enantiomers and/or diastereo-isomers being extremely small. It is shown that the compounds are not optically labile. 3. An attempt has been made to ascertain whether the"crowding" effect of the two nitro substituents on the two carboxyl groups in 3:3'-dinitrodiphenic acid is such as to render the acid sufficiently optically unstable to show first and/or second order asymmetric transformation at room temperature. No sign of optical instability was apparent in the dimethyl ester: the acid could notbe obtained pure. 4. The reactivity of certain diphenyl derivatives with a variety of reagents has been investigated. 5. The ultraviolet absorption spectra of certain diphenyls containing the 7-membered ring bridging the 2:2' positions have been determined, in order to find out how much reliance can be placed on the previous assumption that such spectra are a valuable guide to configuration in the diphenyl series. It is shown that the ultra-violet absorption spectrum of a substituted diphenyl must be used with considerable reserve as a criterion of coplanarity or otherwise.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Organic Chemistry