Photooxidations of alkenes in fluorinated constrained media: Fluoro-organically modified NaY as improved reactors for singlet oxygen “ene” reactions

Abstract

Creating a stationary fluorinated environment inside the zeolite cavity can increase the reactivity observed for intrazeolite photooxidation of alkenes. Exchanging the zeolite with fluorinated organic cations is a much more effective strategy than simply using a fluorinated solvent for slurry irradiations. Use of cations containing C-F bonds is also more efficient than use of deuterated cations for creation of a singlet oxygen friendly environment where the quenching processes are slowed down. Doping the zeolite with fluoro- organic cation 4 resulted in an increase in the singlet oxygen lifetime to 12 μs.