Publication

The effect of an alkoxy group on the kinetic and thermodynamic acidity of benzene and toluene

Manfred Schlosser
1998
Journal Articles

Abstract

2-, 3- And 4-Methoxytoluene can be selectively metalated at an O-adjacent ortho position when butylithium or tert-butyllithium in the presence of sodium (potassium) tert-butoxide or N,N,N',N",N"-pentamethyldiethylenetriamine are employed as reagents. In contrast, lithium diisopropylamide or lithium 2,2,6,6-tetramethylpiperidide deprotonate the benzylic a-position of 2- and 3-methoxytoluene exclusively and of 4-methoxytoluene preferentially. These relative reactivities can be rationalized by an interplay of transition state stabilizing and destabilizing forces (dipole matching and metal coordination vs. lone pair repulsion). [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/f3557343-164f-44be-8744-9d9a13f23e90

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Manfred Schlosser
1998
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/f3557343-164f-44be-8744-9d9a13f23e90

About this result

Related concepts (31)

Organolithium reagent

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers.

Lone pair

In chemistry, a lone pair refers to a pair of valence electrons that are not shared with another atom in a covalent bond and is sometimes called an unshared pair or non-bonding pair. Lone pairs are found in the outermost electron shell of atoms. They can be identified by using a Lewis structure. Electron pairs are therefore considered lone pairs if two electrons are paired but are not used in chemical bonding. Thus, the number of electrons in lone pairs plus the number of electrons in bonds equals the number of valence electrons around an atom.

Coordination complex

A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the coordination centre, and a surrounding array of bound molecules or ions, that are in turn known as ligands or complexing agents. Many metal-containing compounds, especially those that include transition metals (elements like titanium that belong to the periodic table's d-block), are coordination complexes. Coordination complexes are so pervasive that their structures and reactions are described in many ways, sometimes confusingly.

Related publications (2)

The effect of an alkoxy group on the kinetic and thermodynamic acidity of benzene and toluene

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