Electrophilic fluorination of diazoketones

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.