Air. -Since a 9-hydroxyfluorenyl derivative such as (II) is observed as by-product in the reduction of a pyrrolidine-2,5-dione such as (I), the process is investigated in detail. Optimized conditions under air allow the preparation of various 9-hydroxyfluorenes as important building blocks of pharmaceutical drugs. Product (VId) is not available, even after 24h. Some simple fluorenyl compounds are also subjected to the reduction/oxidation procedure. In the case of educt (XIII), the corresponding alcohol and 9-methyl--9H-fluorene (XV), the same dimer (XIV) is formed. The alcohol produces an additional complex mixture, whereas the target (XVI) is formed as second product from (XV). A slight change in the conditions including an oxygen atmosphere allows the exclusive isolation of the desired hydroxy component. -(MATVIIUK, T.; MENENDEZ, C.; CARAYON, C.; SAFFON, N.; VOITENKO, Z.; LHERBET*, C.; BALTAS, M.; Eur.
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