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This reaction goes by the German name Phenolverkochung ("cooking down to yield phenols"). The phenol formed may react with the diazonium salt and hence the reaction is carried in the presence of an acid which suppresses this further reaction. [33] A Sandmeyer-type hydroxylation is also possible using Cu 2 O and Cu 2+ in water.
The Griess diazotization reaction, on which the Griess reagent relies, was first described in 1858 by Peter Griess. [1] [2] The test has also been widely used for the detection of nitrates (N-oxidation state = 5+), which are a common component of explosives, as they can be reduced to nitrites (N-oxidation state = 3+) and detected with the ...
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.
The Pschorr cyclization is a name reaction in organic chemistry, which was named after its discoverer, the German chemist Robert Pschorr (1868-1930). It describes the intramolecular substitution of aromatic compounds via aryldiazonium salts as intermediates and is catalyzed by copper. The reaction is a variant of the Gomberg-Bachmann reaction. [1]
The reaction process begins with diazotization of the amine by nitrous acid. The diazonium group is a good leaving group, forming nitrogen gas when displaced from the organic structure. This displacement can occur via a rearrangement (path A), in which one of the sigma bonds adjacent to the diazo group migrates. This migration results in an ...
The most commonly employed Sandmeyer reactions are the chlorination, bromination, cyanation, and hydroxylation reactions using CuCl, CuBr, CuCN, and Cu 2 O, respectively. More recently, trifluoromethylation of diazonium salts has been developed and is referred to as a 'Sandmeyer-type' reaction.
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.
Diazo compounds have two main Lewis structures in resonance: R 2 >C − –N + ≡N and R 2 >CH=N + =N −. In organic chemistry, the diazo group is an organic moiety consisting of two linked nitrogen atoms at the terminal position.