Synthesis of Fluorinated Cycloalkyl N ‐Phenylcarbamates and Their Microbial Defluorination/Oxygenation by Beauveria bassiana

Earlier investigations showed that cycloalkyl N ‐phenylcarbamates were hydroxylated by the fungus Beauveria bassiana predominantly in the 4‐position relative to the electron‐rich substituent. In cases involving fluorinated methylene groups potentially capable of hydroxylation, however, defluorination and formation of a ketone was observed. The formation of the ketone can be explained by primary hydroxylation to form an unstable geminal fluorohydrin, which is subsequently dehydrofluorinated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)