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The Infrared Spectra of Monosubstituted Biphenyls

Volume 19, Number 1 (Jan. 1965) Page 34-35

Cazes, Jack


As part of a study of the mechanism of free radical phenylation of aromatic compounds it was necessary to obtain analytically pure standards of several biphenyls which were expected products of the reactions being examined. While most of them could be purchased or readily synthesized by standard, unambiguous methods, two of them could not, these being 2-tert-butylbiphenyl and 3-tert-butylbiphenyl. These two standards were obtained via preparative-scale gas chromatographic separation of a mixture containing biphenyl and 2-, 3-, and 4-tert-butylbiphenyl. After ascertaining that each tert-butylbiphenyl fraction collected was pure, it was necessary to determine which isomeric structure belonged to each fraction. Infrared spectroscopy was chosen because of its simplicity, reliability, and the ready availability of spectra of model compounds.