Synthesis of cyclopentadienone epoxides from 10-oxatricyclodecadienones
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Houwen-Claassen,Klunder,Zwanenburg
p. 7134 - 7148
(2007/10/02)
AN ORGANOMETALLIC ROUTE TO (+/-)-3-p-TOLUENESULFINYL-2-PYRONE
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.
Posner, Gary H.,Harrison, Wayne
p. C27 - C30
(2007/10/02)
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