Preparations of SF5- and CF3-substituted arenes utilizing the 7-oxabicyclo[2.2.1]hept-2-ene synthones

Abstract

The synthesis of SF₅- and CF₃-substituted benzenes and naphthalenes from various 7-oxanorbornene derivatives utilizing SF₅Cl and CF₃I radical addition reactions, followed by dehydrohalogenation and aromatization, is reported. The differences in the behavior of the SF₅- and CF₃-containing intermediates under basic and acidic conditions are discussed. The experimentally observed high regioselectivities of the formation of 2-R_F-substituted-1-naphthols agree well with the ab initio computations, revealing the first example of the SF₅⋯HO hydrogen bonding.