Journal
ORGANIC LETTERS
Volume 13, Issue 18, Pages 4846-4849Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol201922u
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Funding
- NIH-NIGMS [5SC1GM084776]
- NIH [GM6133, GM08228]
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Resveratrol (1) reacts with singlet oxygen by two major pathways: A [2 + 2] cycloaddition forming a transient dioxetane that cleaves into the corresponding aldehydes and a [4 + 2] cycloaddition forming an endoperoxide that, upon heating, undergoes a rearrangement to moracin M. The rate constant by which singlet oxygen is removed by 1(k(T)) was determined by time-resolved infrared luminescence spectroscopy to be 1.5 x 10(6) M-1 sec(-1) in CD3OD, smaller than previously reported values. Chemical reaction accounts for ca. 25% of k(T).
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