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After the German chemist August Kekulé and his Belgian student Antoine Paul Nicolas Franchimont (1844–1919) first synthesized triphenylmethane in 1872, [2] the Russian doctoral student Walerius Hemilian (1851–1914) first synthesized triphenylmethanol in 1874 by reacting triphenylmethyl bromide with water as well as by oxidizing triphenylmethane.
The triphenylmethyl substituent, also called trityl after 1927 suggestion by Helferich et al. [7], is widely used in organic chemistry. Trityl serves as a protecting group for alcohols. [8] protection (requires proton acceptor): Ph 3 CCl + ROH → Ph 3 COR + HCl deprotection: Ph 3 COR + HBr → ROH + Ph 3 CBr
Gomberg's dimer can be prepared quantitatively by treating trityl bromide with powdered copper or silver: [2] 2 Ph 3 CBr + 2 Cu → Ph 2 C=C 6 H 5 -CPh 3 + 2 CuBr Gomberg's dimer reversibly dissociates to the triphenylmethyl radical in organic solvents: [ 3 ]
Methyltriphenylphosphonium bromide is produced by treating triphenylphosphine with methyl bromide: [1] Ph 3 P + CH 3 Br → Ph 3 PCH 3 Br. Methyltriphenylphosphonium bromide is the principal precursor to methylenetriphenylphosphorane, a useful methylenating reagent. This conversion is achieved by treating methyltriphenylphosphonium bromide with ...
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C 6 H 5) 3 and often abbreviated to P Ph 3 or Ph 3 P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry.
Triphenylamine is an organic compound with formula (C 6 H 5) 3 N. In contrast to most amines, triphenylamine is nonbasic.At room temperature it appears as a colorless crystalline solid, with monoclinic structure.
The triphenylmethyl radical (often shortened to trityl radical after 1927 suggestion by Helferich et al. [1]) is an organic compound with the formula (C 6 H 5) 3 C. It is a persistent radical . It was the first radical ever to be described in organic chemistry .
Gomberg's classical organic synthesis shown below starts by reacting triphenylmethyl bromide 1 with phenylhydrazine 2 to the hydrazine 3. Oxidation with nitrous acid then produces the azo compound 4 from which on heating above the melting point, nitrogen gas evolves with formation of tetraphenylmethane 5.