Publication

The acidifying effects of chlorine and bromine: little difference

Manfred Schlosser
1997
Journal Articles

Abstract

Lithium diisopropylamide deprotonates o- and p-bromochlorobenzene randomly at the two halogen adjacent positions. Obviously for steric reasons, the bulkier base lithium 2,2,6,6-tetramethylpiperidide favors the attack in the vicinity of the chlorine rather than the bromine atom to the extent of 2:1. At -75 DegC, both 2-bromo-3-chlorophenyllithium and 3-bromo-2-chlorophenyllithium isomerize to give 2-bromo-6-chlorophenyllithium. The latter species can be directly generated from 1-bromo-3-chlorobenzene. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/c72bc359-966d-4573-9c94-f6f35a2b5086

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Manfred Schlosser
1997
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/c72bc359-966d-4573-9c94-f6f35a2b5086

About this result

Related concepts (14)

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.

Bromine

Bromine is a chemical element with the symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig (in 1825) and Antoine Jérôme Balard (in 1826), its name was derived from the Ancient Greek βρῶμος (bromos) meaning "stench", referring to its sharp and pungent smell.

Organosodium chemistry

Organosodium chemistry is the chemistry of organometallic compounds containing a carbon to sodium chemical bond. The application of organosodium compounds in chemistry is limited in part due to competition from organolithium compounds, which are commercially available and exhibit more convenient reactivity. The principal organosodium compound of commercial importance is sodium cyclopentadienide. Sodium tetraphenylborate can also be classified as an organosodium compound since in the solid state sodium is bound to the aryl groups.