Reaction of singlet oxygen with trans-4-propenylanisole. Formation Of |
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| Authors: | Greer Vassilikogiannakis Lee Koffas Nahm Foote |
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| Affiliation: | Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, USA. |
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| Abstract: | 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. |
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