Mamuye, Ashenafi Damtew (2015) New perspectives and applications in organolithium chemistry: halocarbenoids and reductive lithiation. Doctoral Thesis.
We report on the employment of 2-methyltetrahydrofuran and cyclopentyl methyl ether as alternative green solvents for the efficient generation of radical anions of Polycyclic Aromatic Hydrocarbons and their employment in the generation of organolithium reagents. 2-MeTHF was successfully employed as a solvent in the reductive lithiation of the benzylic C–O bond of phthalan, of the aromatic C–Cl bond of 4-chlorobenzyl methyl ether, and of the C–N bond of N-phenylaziridine. Results obtained with N-phenylaziridine show that such a PAH mediated reductive lithiation of is strongly dependant on the solvent employed.
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