CCXIII.—The molecular configurations of polynuclear aromatic compounds. Part IV. 6 : 6′-Dichlorodiphenic acid; its synthesis and resolution into optically active components

Recent Progress in Stereochemistry.

“…There is unusual stereochemical interest in the interference measurements of Debye and Bewilogua (195) made with simple substituted methane derivatives, for they permit a statement in regard to the form of the tetrahedron. As table 11 shows, the distance between the chlorine atoms increases with the decrease of their number, which may indicate a spreading of the valences (184). Wierl obtained practically identical figures from the diffraction of cathode rays.…”

The Stereochemistry of Diphenyls and Analogous Compounds.

“…The compounds previously resolved were limited to those containing nitro and carboxyl groups. Christie, James, and Kenner (40), by resolving 2,2'-dichloro-6,6'-dicarboxydiphenyl (LII), showed that no specific effect of the nitro group was involved and somewhat later Kenner and . A. Turner (72) obtained active forms of 2,2'-dimethoxy-6,6'-dicarboxydiphenyl (LIII).…”

“…Certain compounds not mentioned in the previous discussion because they have no bearing on the theoretical aspects of the problem have been included. (41) 2,4,2', 4'-Tetranitro-6,6'-dicarboxydiphenyl (41) 2,2',4-Trinitro-6,6'-dicarboxydiphenyl (43) 2,2'-Dichloro-6,6'-dicarboxydiphenyl (40) 2,2'-Dimethoxy-6,6'-dicarboxydiphenyl (72,161) 2,2'-Difluoro-6,6'-dicarboxydiphenyl (161) 2,2'-Dinitro-4,4'-dicarboxy-6,6'-dichlorodiphenyl (68) T h i s c o n t e n t i s…”

Potential organ or tumor imaging agents. 11. Radioiodinated tyramines

“…The successful synthesis of 3 suggested that a similar synthetic approach would be suitable for the preparation of 2-(3-hydroxy-5-iodophenyl)ethylamine (4). The most suitable and most readily available starting material for this synthesis was 3-iodo-5-nitrobenzoic acid (12). Thus, initial efforts were directed toward the conversion of the starting benzoic acid 12 to 3-benzyloxy-5-iodobenzyl cyanide (20).…”