FLUORINATION WITH XENON DIFLUORIDE .21. EVIDENCE FOR FREE-RADICAL INTERMEDIATES IN TRIFLUOROACETIC-ACID CATALYZED FLUORINATIONS

Trifluoroacetic acid catalyzed fluorination of styrene with xenon difluoride resulted in the formation of five products: 1-fluoro-1-phenyl-2-(trifluoromethyl)ethane (2), 1,2-difluoro-1-phenylethane (3), 1-(trifluoroacetoxy)-1-phenyl-2-(trifluoromethyl)ethane (4), 1-(trifluoroacetoxy)-1-phenyl-2-fluoroethane (5), and 1-fluoro-1-phenyl-2-(trifluoroacetoxy)ethane (6). The reaction with diphenylacetylene resulted in the formation of six products. The formation of fluoro radicals, trifluoromethyl radicals, and trifluoroacetoxy radicals, formed by decomposition of FeXeOCOCF3, is suggested in order to explain the formation of products. © 1979 American Chemical Society.