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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.

zeitschrift für naturforschung b

Impulsphotolytische Untersuchungen zum Mechanismus der photochemischen WoLFF-Umlagerung.: Flash Light Photolytic Investigations Concerning the Mechanism of the Photochemical WOLFF Rearrangement