Substitutions in Positions 2 and 2´ of C2-Symmetric Binaphthyl Derivatives. Substitution Reactions of Aromatic Compounds with Stereochemical Aspects

Page: 353

M. Putala

Department of Organic Chemistry, Faculty of Natural Science, Comenius University, Bratislava, Slovak Republic


The review deals with a unique type of substitution reactions of aromatic compounds in which retention of configuration is questionable, namely with substitutions in positions 2 and 2´ of C2-symmetric 2,2´-disubstituted 1,1´-binaphthyl derivatives. The stereochemical aspect results from the fact that the nonbonding interaction of substituents in positions 2 and 2´ (where bond formation and breaking occur in the course of substitution) is decisive for configuration stability of these axial chiral compounds. As a rule, the mentioned reactions proceed stereoconservatively (with retention of spatial arrangement of the binaphthyl moiety) if there is no mutual bonding interaction in positions 2 and 2´ in the course of the reaction.


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