Abstract
3-Bromo-2-pyrone reacts with dimethylcopperlithium and then with p-tolyl p-toluenethiosulfonate to form 3- p-toluenethio-2-pyrone. Organocopper species are likely intermediates in this reaction. Oxidation of the sulfide produces (±)-3- p-toluenesulfinyl-2-pyrone. The overall process involves an important and useful umpolung, a reversal of reactivity at C(3) of the pyrone ring from an electrophilic center to a nucleophilic center.
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