Publication

Acidity enhancement through homoconjugation: selective introduction of sodium into olefinic positions

Manfred Schlosser
1985
Journal Articles

Abstract

When treated with BuLi and Me3CONa, both norbornadiene and norbornene underwent a H/Na-exchange at the 2-position. The diene, however, reacted approx. 30 times faster with Me3SiCl. Bicyclo[3.2.0]hepta-2,6-diene was also more readily metalated than bicyclo[3.2.0]hept-6-ene and its 7-position was preferentially attacked. Under the same conditions, cycloheptatriene was silylated at the 2-position only. [on SciFinder (R)]

Official source

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Manfred Schlosser
1985
Journal Articles

Abstract

Official source

Related concepts (21)

Ion exchange

Ion exchange is a reversible interchange of one kind of ion present in an insoluble solid with another of like charge present in a solution surrounding the solid with the reaction being used especially for softening or making water demineralised, the purification of chemicals and separation of substances. Ion exchange usually describes a process of purification of aqueous solutions using solid polymeric ion-exchange resin. More precisely, the term encompasses a large variety of processes where ions are exchanged between two electrolytes.

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.

Metal–halogen exchange

In organometallic chemistry, metal–halogen exchange is a fundamental reaction that converts an organic halide into an organometallic product. The reaction commonly involves the use of electropositive metals (Li, Na, Mg) and organochlorides, bromides, and iodides. Particularly well-developed is the use of metal–halogen exchange for the preparation of organolithium compounds. Two kinds of lithium–halogen exchange can be considered: reactions involving organolithium compounds and reactions involving lithium metal.