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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.
In the reaction mechanism for this reaction, the diazo compound reacts as a 1,3-dipole in a 1,3-dipolar cycloaddition with the thioketone to give a 5-membered thiadiazoline ring. This intermediate is unstable; it extrudes a molecule of nitrogen to form a thiocarbonyl ylide, which then cyclizes to form a stable episulfide.
The Gomberg–Bachmann reaction, named for the Russian-American chemist Moses Gomberg and the American chemist Werner Emmanuel Bachmann, is an aryl -aryl coupling reaction via a diazonium salt. [1][2][3] The arene compound (here benzene) is reacted with a diazonium salt in the presence of a base to provide the biaryl through an intermediate ...
A simple dialkyl diazo compound is diethyldiazene, CH 3 CH 2 −N=N−CH 2 CH 3, which can be synthesized through a variant of the Ramberg–Bäcklund reaction. [7] Because of their instability, aliphatic azo compounds pose the risk of explosion. AIBN is produced by converting acetone cyanohydrin to the hydrazine derivative followed by ...
Diazo. In organic chemistry, the diazo group is an organic moiety consisting of two linked nitrogen atoms at the terminal position. Overall charge-neutral organic compounds containing the diazo group bound to a carbon atom are called diazo compounds or diazoalkanes[a] and are described by the general structural formula R2C=N+=N−.
The first step of the Bamford–Stevens reaction is the formation of the diazo compound 3. [4] The mechanism of the Bamford-Stevens reaction. In protic solvents, the diazo compound 3 decomposes to the carbenium ion 5. The mechanism of the Bamford-Stevens reaction. In aprotic solvents, the diazo compound 3 decomposes to the carbene 7. The ...
The Griess test involves two subsequent reactions. When sulfanilamide is added, the nitrite ion reacts with it in the Griess diazotization reaction to form a diazonium salt, which then reacts with N- (1-naphthyl)ethylenediamine in an azo coupling reaction, forming a pink-red azo dye. Using a spectrophotometer, it is possible to quantitatively ...
Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N-C linkage. [1] Azo dyes are synthetic dyes and do not occur naturally. [2][3] Most azo dyes contain only one ...