Selective catalytic carbanionic ethylation of methylphenols: influence of catalyst and substitution pattern |
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Authors: | Barry R Steele Carolina Villalonga-Barber Maria Micha-Screttas Constantinos G Screttas |
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Institution: | Institute of Organic and Pharmaceutical Chemistry, National Hellenic Research Foundation, Vas. Constantinou Ave. 48, Athens 116 35, Greece |
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Abstract: | Addition of ethylene to the carbanions formed by the metallation of the lithium salts of di- and trimethylphenols by the strongly basic system, n-BuLi-LiK(OCH2CH2NMe2)2 provides a useful synthetic route to a range of alkylphenols. The ease of alkylation of the methyl groups decreases in the order ortho>meta>para while the inclusion of Mg(OCH2CH2OEt)2 in the catalyst restricts alkylation to the methyl groups ortho to the hydroxy group. Dialkylation occurs only at the ortho-methyl groups and only if the adjacent meta-position is unsubstituted. The potential of these products for the synthesis of sterically hindered ligands is outlined. |
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Keywords: | Bulky aromatic Organolithium Phenol Superbase Metallation Carbometalation Schiff base Catalysis Lipophilic |
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