Publication

Relative carbanion basicities as driving force for an intramolecular silyl migration of lithiated biphenyls

Rosario Scopelliti
2007
Journal Articles

Abstract

A solvent-dependent silyl migration of lithiated biphenyls is described, involving the intermediate formation of a pentacoordinated silicate complex. Differences in the relative basicities of the aryllithium intermediates are the possible driving force for this migration. (c) 2007 Elsevier Ltd. All rights reserved.

Official source

https://infoscience.epfl.ch/entities/publication/2ed747db-742a-433a-ac98-dd16b64bb00b

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Rosario Scopelliti
2007
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/2ed747db-742a-433a-ac98-dd16b64bb00b

About this result

Related concepts (9)

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.

Carbanion

In organic chemistry, a carbanion is an anion in which carbon is negatively charged. Formally, a carbanion is the conjugate base of a carbon acid: where B stands for the base. The carbanions formed from deprotonation of alkanes (at an sp3 carbon), alkenes (at an sp2 carbon), arenes (at an sp2 carbon), and alkynes (at an sp carbon) are known as alkyl, alkenyl (vinyl), aryl, and alkynyl (acetylide) anions, respectively.

N-Butyllithium

n-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry. Butyllithium is commercially available as solutions (15%, 25%, 1.5 M, 2 M, 2.5 M, 10 M, etc.) in alkanes such as pentane, hexanes, and heptanes.

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