PHOTOOXIDATION OF SULFENIC ACID-DERIVATIVES .4. REACTIONS OF SINGLET OXYGEN WITH SULFENAMIDES

The reactions of singlet oxygen with nine sulfenamides are reported. A detailed kinetic study reveals that two intermediates are required on the photooxidation reaction surface. One intermediate acts as a nucle ophile and the second intermediate as an electrophile in their reactio ns with diaryl sulfoxides and diaryl sulfides, respectively. Physical quenching is also suppressed in the sulfenamides relative to other sul fur-containing singlet oxygen substrates, The mechanism of the reactio n is discussed and compared to diethyl sulfide photooxidation, and a r ationale for the decreased importance of physical quenching in these s ubstrates is presented.