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Synlett 1993; 1993(3): 233-234
DOI: 10.1055/s-1993-22415
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Oxidation of Carbanions with Lithium tert-Butyl Peroxide

Marc Julia* , Virginie Pfeuty Saint-Jalmes, Jean-Noël Verpeaux
  • *Département de Chimie de l'Ecole Normale Supérieure, U.R.A. CNRS 1110, 24 rue Lhomond, F-75231 Paris Cédex 05, France
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Publication History

Publication Date:
19 March 2002 (online)

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Lithium t-butyl peroxide reacts with several carbanions, leading to the corresponding alcohols via oxygen transfer. Lithiated arenes can be converted into phenols. An easy and convenient preparation of ynolates opening the way to ketenes, esters or silyl ynol ethers from acetylides is reported. Lithiated hydroperoxides display an electrophilic behaviour at oxygen that can be compared with the electrophilic properties of carbenoids.