STEREOCHEMISTRY OF DIPHENYL. XXIV.¹ PREPARATION AND PROPERTIES OF 2,2'-DIFLUORO-3,3'-DICARBOXY-6,6'-DIMETHOXYDIPHENYL

Abstract

with each alkaloid could be isolated. Each of the salts mutarotated to equilibrium values which were equal mixtures of the two diastereoisomeric salts. Strychnine gave a salt which showed no mutarotation and yielded no active acid.3. By careful decomposition with hydrochloric acid, the Z-acid was isolated. It racemized rapidly in organic solvents. The sodium salt racemized much more rapidly in absolute alcohol than in water. Urbana, Illinois

The Stereochemistry of Diphenyls and Analogous Compounds.

“…It has been pointed out by Carothers (34) and by Mascarelli (117) that an objection to the Kaufler formula which has never 9 Information from an expert in benzidine dyes is that benzidinetetrazonium salts give in some instances soluble monocoupled products. As a consequence the question as to this characteristic of benzidinetetrazonium salts may be considered as still lacking satisfactory explanation.…”

“…Nonresolvable 2,2' ,6,6'-tetrasubstituted compounds (A). The following representatives of Type A (LXXXIV, LXXXV, LXXXVI, LXXXVII), have been prepared by Adams and his students (77,49,9), and their resolution has been attempted by means of various alkaloid salts-brucine, strychnine, morphine, cinchonine, and quinine. In no instance was more than a single salt obtained and none of these showed mutarotation even at low temperatures or gave an active acid on decomposition.…”

Addition of dichlorocarbene to oxyberberine and berberine

“…O-Demethylation at C-9 for berberinium salts and their C-8 oxy analogues in the presence of acid is a well-established reaction. 4 It is clear, therefore, that adduct 5 can undergo such a demethylation to supply phenol 9 which can in turn be converted to aldehyde 10.…”