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 nucleophile and the second intermediate as an electrophile in their reactions with diaryl sulfoxides and diaryl sulfides, respectively. Physical quenching is also suppressed in the sulfenamides relative to other sulfur-containing singlet oxygen substrates, The mechanism of the reaction is discussed and compared to diethyl sulfide photooxidation, and a rationale for the decreased importance of physical quenching in these substrates is presented.