Syntheses and reactions of 10-(2,2'-biphenylylene)-9-phenanthrone derivatives and some consideration of ethyl isomers in their analogous series.

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The Wagner-Meerwein rearrangement of 9′-methyl-9,9′-bifluoren-9-ol yielded 10-(2,2′-biphenylylene)-9-methylenephenanthrene. Ozonolysis of the phenanthrene afforded 10-(2,2′-biphenylylene)-9-phenanthrone. This pinacolone was converted into 2′-(9-fluorenyl)biphenyl-2-carboxylic acid. Oxidation of 4,9′-bifluoren-9-one, which was obtained by ring closure of the acid, gave 9′-hydroxy-, 9′-benzyl-, and 9′-benzyloxy-4,9′-bifluoren-9-one. Isomers of 2,2′-diethyl-9,9′-bifluorene-9,9′-diol were obtained by reduction of 2-ethyl-9-fluorenone. The pinacols were rearranged to the corresponding pinacolones, which were cleaved into carboxylic acids. The structural assignment of these isomers was made by spectral analyses.
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