Photooxidations of alkenes in fluorinated constrained media: fluoro-organically modified NaY as improved reactors for singlet oxygen "Ene" reactions

J Org Chem. 2007 Mar 30;72(7):2644-6. doi: 10.1021/jo0625047. Epub 2007 Mar 1.

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 micros.