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Electrophilic substitution reactions are chemical reactions in which an electrophile displaces a functional group in a compound, which is typically, but not always, aromatic. Aromatic substitution reactions are characteristic of aromatic compounds and are common ways of introducing functional groups into benzene rings.
In organic chemistry, an azo coupling is an reaction between a diazonium compound (R−N≡N +) and another aromatic compound that produces an azo compound (R−N=N−R’).In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile, and the activated carbon (usually from an arene, which is called coupling agent), serves as a nucleophile.
Directed ortho metalation (DoM) is an adaptation of electrophilic aromatic substitution in which electrophiles attach themselves exclusively to the ortho-position of a direct metalation group or DMG through the intermediary of an aryllithium compound. [1] The DMG interacts with lithium through a hetero atom.
Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic. Detailed understanding of a reaction type helps to ...
Electrophilic nitrogen sources are, however, either toxic or explosive in general. Great care should be taken while handling these reagents. Many electrophilic nitrogen sources do not provide amines immediately, but a number of methods exist to generate the corresponding amines. Tosylamines: tributyltin hydride; Azo compounds: H 2 /Pd
In organic chemistry, an electrophilic aromatic halogenation is a type of electrophilic aromatic substitution.This organic reaction is typical of aromatic compounds and a very useful method for adding substituents to an aromatic system.
Sulfur trioxide or its protonated derivative is the actual electrophile in this electrophilic aromatic substitution. To drive the equilibrium, dehydrating agents such as thionyl chloride can be added: [2] C 6 H 6 + H 2 SO 4 + SOCl 2 → C 6 H 5 SO 3 H + SO 2 + 2 HCl. Historically, mercurous sulfate has been used to catalyze the reaction. [3]
The Haworth synthesis is a classic method for the synthesis of polycyclic aromatic hydrocarbons. In this reaction, an arene is reacted with succinic anhydride, the subsequent product is then reduced in either a Clemmensen reduction or a Wolff-Kishner reduction. Lastly, a second Friedel-Crafts acylation takes place with addition of acid.