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• W1548976682 abstract "Metalation of mesitylene with butyllithium in hexane in the presence of tetramethylethylenediamine yields mono-, di- and trilithiated benzylic compounds (1–5), characterized as their silylated derivatives. Dilithiation occurred partly at the same but preferentially at different methyls. The symmetrical tris-1,3,5-(lithiomethylene)benzene was the main product. Similar metalation occurred with m-xylene. o-Xylene gave also dilithiated products, but at a slower rate, and p-xylene gave slowly and exclusively the gem-dilithio-derivative. The results were explained by greater stabilization of polylithio derivatives with charges all on the starred carbons of the conjugated system, rather than those with charges uniformly dispersed on all carbons. CNDO/2 calculations of the energy of the anions account only partially for the order of stability of most of the studied compounds, but a good correlation between this experimental order and the energies of the lithium compounds was found." @default.
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• W1548976682 date "1976-01-01" @default.
• W1548976682 modified "2023-10-11" @default.
• W1548976682 title "Metalations—XVI" @default.
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• W1548976682 doi "https://doi.org/10.1016/0040-4020(76)80020-8" @default.
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