Studies in diphenyls and dinaphthyls

Abstract

The first section of this thesis deals with the synthesis of some derivatives of a substituted diphenic acid with seven membered bridges across the 2:2'- positions. It was hoped to obtain these compounds in optically active forms also. This was, however, not found possible as the 4:4':6:6'-tetrachlorodiphenic acid from which the above compounds were derived could not be resolved into optically pure isomers. The ultra-violet absorption spectra of these compounds were studied in order to investigate the relation between conjugation and configuration in the diphenyls and the results lend further support to the conclusions drawn by other workers in this field. A new series of compounds were prepared from 2:2'-dinaphthyl-3:3,-dicarboxylic acid with the view to resolving the azepinium salt: obtained from it. This salt and the dinaphthyl oxepin both have a seven membered ring. The study of the ultra-violet absorption spectra of these compounds provide basically important spectral data for the dinaphthyls. In the next section are described the attempts to prepare dialdehyde-2:2'-diphenyl which would have provided a starting material for many interesting syntheses but the yield of the dialdehyde was low and its preparation presented considerable practical difficulties.2:2'-Diacyldiphenyls are known to give anomalous results on reduction and 2:2'-dipropionyldiphenyl was prepared to study the effect of different reducing agents on it. 9:10-Diethylphenanthrene and 2:2'-bis-B-methylethenyl-diphenyl were obtained from it in good yields. The ultra-violet absorption spectrum of this unsaturated hydrocarbon was also studied.