Reaction of singlet oxygen with trans-4-propenylanisole. Formation Of
We report the effects of added acid in the reaction of singlet oxygen with trans-4-propenylanisole (1). We provide evidence that solvent acidity modifies the behavior of the transient intermediates. Relative to reactions in aprotic solvent, enhanced dioxetane concentrations are observed in MeOH and in nonprotic solvents with acid. We suggest a new mechanism that invokes a proton transfer from MeOH and benzoic acid to perepoxide (2) and zwitterion (3) intermediates.
Greer
A
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA.
Vassilikogiannakis
G
Lee
KC
Koffas
TS
Nahm
K
Foote
CS