
The configuration of cis-2-hydroxy-2-phenyl-cyclohexanecarboxilic acid (cicloxilic acid) was deduced by comparing its NMR and IR spectra with those of its diastereoisomer and of their respective analogs, the 1-hydroxy(bicyclohexyl)-2-carboxylic acids. The diastereoisomer was prepared by converting cicloxilic acid to the corresponding 2-chloro-2-phenyl-cyclohexanecarboxylic acid and subsequent hydrolysis of the latter with aqueous solvents in the presence of wet silver oxide, or by simple solvolysis. The pair of 1-hydroxy(bicyclohexyl)-2-carboxylic acid was prepared from the respective phenylic terms by catalytic hydrogenation. Comparison of the NMR spectra revealed the spatial arrangement of the -H and -COOH groups on the carbon-alpha atom and the study of the interaction between the substitutents -OH and -COOH by IR spectrography revealed the position of the -OH group with respect to the -COOH group, as a result of which the configuration and conformation of the compounds under study were established. Cicloxilic acid is thus represented by the steric formula 4.
Chemistry, Chemical Phenomena, Cyclohexanecarboxylic Acids, Molecular Conformation, Stereoisomerism
Chemistry, Chemical Phenomena, Cyclohexanecarboxylic Acids, Molecular Conformation, Stereoisomerism
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