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Substrates containing two phenols (or an aniline and a phenol; see equation (8) below for a related example), undergo oxidative coupling in the presence of hypervalent iodine(III) reagents. Coupling of both the ortho and para positions is possible; however, the use of bulky silyl-protected phenols provides complete selectivity for para coupling ...
Once the imine is produced, it reacts with phenol in the presence of water to yield an α-aminobenzylphenol. An electron pushing mechanism for the Betti Reaction. First, the lone-pair on the nitrogen of the imine deprotonates the phenol, pushing the bonding electrons onto the oxygen.
An alternative mechanism is based on the aniline and the aldehyde forming at first the Schiff base upon water elimination. The subsequent reaction with the enol form of pyruvic acid ( 1 ) leads to the formation of the above-mentioned aniline derivative ( 3 ) followed by the above-described reaction mechanism: [ 4 ]
In chemistry, ammonolysis (/am·mo·nol·y·sis/) is the process of splitting ammonia into + +. [1] Ammonolysis reactions can be conducted with organic compounds to produce amines (molecules containing a nitrogen atom with a lone pair, :N), [2] or with inorganic compounds to produce nitrides.
The hydroxide will also deprotonate the phenol (4) to give a negatively charged phenoxide (5). The negative charge is delocalised into the aromatic ring, making it far more nucleophilic. Nucleophilic attack on the dichlorocarbene gives an intermediate dichloromethyl substituted phenol (7). After basic hydrolysis, the desired product (9) is formed.
Vanadium tetrachloride is known to effect one-electron oxidations, which is invoked in this conversion. [2] Oxidative coupling of phenol by VCl 4. Coproducts including vanadium(III) and hydrogen chloride are not shown. Oxidative phenol couplings can occur through either inner sphere or outer sphere processes. In inner sphere processes, the ...
Protonated hexamine ring-opens to expose an iminium group. Addition to the aromatic ring results in an intermediate at the oxidation state of a benzylamine. An intramolecular redox reaction then ensues, raising the benzylic carbon to the oxidation state of an aldehyde. The oxygen atom is provided by water on acid hydrolysis in the final step.
Formyl functional group is shown in blue. Formylation refers to any chemical processes in which a compound is functionalized with a formyl group (-CH=O). In organic chemistry, the term is most commonly used with regards to aromatic compounds (for example the conversion of benzene to benzaldehyde in the Gattermann–Koch reaction).