Abstract
The parent hydrocarbons benzene and naphthalene have a poor kinetic acidity and attempts at metallation using alkyllithium in THF or Et2O result only in attack on the solvent. Quantitative conversion into phenyllithium can be effected however, if a large excess of benzene is allowed to react with BuLi · TMEDA in hexane at reflux temperature [9, 167]. In the case of naphthalene this metallation procedure has no practical importance, because 1- and 2-naphthyllithium are produced in comparable amounts, along with some dimetallated naphthalene ([9], compare also [160]).
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© 1987 Springer-Verlag Berlin Heidelberg
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Brandsma, L., Verkruijsse, H.D. (1987). Metallated Aromatic Compounds. In: Preparative Polar Organometallic Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-87921-0_7
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DOI: https://doi.org/10.1007/978-3-642-87921-0_7
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-16916-1
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