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These occur between alkenes and electrophiles, often halogens as in halogen addition reactions. Common reactions include use of bromine water to titrate against a sample to deduce the number of double bonds present. For example, ethene + bromine → 1,2-dibromoethane: C 2 H 4 + Br 2 → BrCH 2 CH 2 Br. This takes the form of 3 main steps shown ...
In electrophilic substitution in aromatic compounds, an atom appended to the aromatic ring, usually hydrogen, is replaced by an electrophile.The most important reactions of this type that take place are aromatic nitration, aromatic halogenation, aromatic sulfonation and acylation and alkylating Friedel-Crafts reactions.
A nitrogen bound to both a good electrofuge and a good nucleofuge is known as a nitrenoid (for its resemblance to a nitrene). [2] Nitrenes lack a full octet of electrons are thus highly electrophilic; nitrenoids exhibit analogous behavior and are often good substrates for electrophilic amination reactions.
Electrophilic aromatic substitutions with prochiral carbon electrophiles have been adapted for asymmetric synthesis by switching to chiral Lewis acid catalysts especially in Friedel–Crafts type reactions. An early example concerns the addition of chloral to phenols catalyzed by aluminium chloride modified with (–)-menthol. [6]
Cross electrophile coupling is a type of cross-coupling reaction that occurs between two electrophiles. It is often catalyzed by transition metal catalyst(s). Unlike conventional cross-coupling reactions of an electrophile with an organometallic reagent, [1] the coupling partners in cross electrophile coupling reactions are both electrophiles. [2]
For example, compared to benzene, pyrrole is more rapidly attacked by electrophiles. Pyrrole is therefore considered to be an electron-rich aromatic ring. [ 5 ] Similarly, benzene derivatives with electron-donating groups (EDGs) are attacked by electrophiles faster than in benzene. [ 6 ]
Vicinal difunctionalization refers to a chemical reaction involving transformations at two adjacent centers (most commonly carbons). This transformation can be accomplished in α,β-unsaturated carbonyl compounds via the conjugate addition of a nucleophile to the β-position followed by trapping of the resulting enolate with an electrophile at the α-position.
Below is an example of intramolecular carbolithiation reaction. The lithium species derived from the lithium–halogen exchange cyclized to form the vinyllithium through 5-exo-trig ring closure. The vinyllithium species further reacts with electrophiles and produce functionalized cyclopentylidene compounds. [35]