Direct lithiation of alkoxyphenols: metalation versus demethylation. An experimental and theoretical (MNDO) study

J Morey, A Costa, PM Deya, G Suner…

Index: Morey, Jeroni; Costa, Antoni; Deya, Pere M.; Suner, Guillem; Saa, Jose M. Journal of Organic Chemistry, 1990 , vol. 55, p. 3902 - 3909

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Citation Number: 16

Abstract

The direct lithiation of simple alkoxyphenols has been studied both from a theoretical and an experimental viewpoint. Efficient lithiations were achieved by using a 2: l tBuLi-tBuOLi mixture (LICLIOR) in THF at room temperature. In most cases alkoxy groups are responsible for the regioselectivity observed, although for the case of 2-methoxyphenol both the OMe and OLi groups actually act as ortho-directing groups during lithiation. Demethylation has ...

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