Reductive lithiation of alkyl phenyl sulfides in diethyl ether. A ready access to α,α-dialkylbenzyllithiums |
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Authors: | Constantinos G Screttas Georgios A HeropoulosMaria Micha-Screttas Barry R SteeleDimitrios P Catsoulacos |
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Institution: | Institute of Organic and Pharmaceutical Chemistry, National Hellenic Research Foundation, Vas. Constantinou Avenue 48, Athens 116 35, Greece |
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Abstract: | Diethyl ether is a convenient solvent for the conversion of benzylic phenyl sulfides to the corresponding organolithiums by an uncatalyzed reductive metalation, while catalysis by naphthalene is required to achieve the same reaction for alkyl phenyl sulfides. The addition of magnesium 2-ethoxyethoxide to solutions of unstable alkyllithiums prepared in this way provides storable reagents. |
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Keywords: | lithiation reduction thioethers radical anion magnesium alkoxide |
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