Journal of Organometallic Chemistry p. C27 - C30 (1985)
Update date:2022-08-11
Topics:
Posner, Gary H.
Harrison, Wayne
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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