Electrophilic fluorination of diazoketones

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Abstract
Fluorination of diazoketones with trifluoro(fluoro-oxy)methane produces mainly a mixture of αα-difluoroketones and α-fluoro-α-trifluoromethyoxy ketones. The initial electrophilic attack on the diazo group is followed by nucleophilic attack by F– or CF3O–. In the case of diazocamphor a rearrangement occurs and leads to the formation of a fluorotricyclanone. The use of molecular fluorine can also lead to αα-difluoroketones.