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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 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 R 2 C=N + =N − .
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 reaction of the surface with a solution of diazonium salt in acetonitrile for 2 hours in the dark is a spontaneous process through a free radical mechanism: [42] Diazonium salt application silicon wafer. So far grafting of diazonium salts on metals has been accomplished on iron, cobalt, nickel, platinum, palladium, zinc, copper and gold ...
These reactions entail diazotization of aminocyclobutanes and aminocyclopropanes. Loss of N 2 from the diazo cations results in secondary carbocations, which tend to rearrange and then undergo hydrolysis. The reaction converts aminocyclobutane into a mixture of hydroxycyclobutane and hydroxymethylcyclopropane.
Most azo dyes are prepared by azo coupling, which entails an electrophilic substitution reaction of an aryl diazonium cation with another compound, the coupling partner. Generally, coupling partners are other aromatic compounds with electron-donating groups: [7] ArN + 2 + Ar′H → ArN=NAr′ + H +
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 ...
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.