WOLFF Rearrangement, Flash Light Photolysis, Kinetic Measurements, 9,10-Diazophenantlirone, Diphenylene Ketene 9,10-Diazophenanthrone undergoes WOLFF rearrangement in alcoholic solvents and yields esters of 9-fluorene carboxylic acid. By flash light photolysis four intermediates could be detected. Kinetic measurements showed that the ketene formed by photolysis reacts with the solvent to give a cyclopentadienylic carbanion, which is protonated. A carbene or an oxirene intermediate could not be found.
Diphenyldiazomethane reacts with triphenylborane to yield benzophenonazine and benzophenone triphenylmethylhydrazone. The formation of the latter is elucidated by ESR spectroscopic detection of the triphenylmethyl radical. The reaction can be modified to a simple method for the preparation of triphenylmethyl radicals in high yields.
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