An organometallic route to (±) 3-p-toluenesulfinyl-2-pyrone
GH Posner, W Harrison
Index: Posner, Gary H.; Harrison, Wayne Journal of Organometallic Chemistry, 1985 , vol. 285, p. C27 - C30
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Abstract
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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