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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
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 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 .
The compound achieved fame as the dimer of triphenylmethyl radical, which was prepared by Moses Gomberg in his quest for hexaphenylethane. Its quinoid structure has been determined by X-ray crystallography. The C-C bond that reversibly breaks is rather long at 159.7 picometers. [1]
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 ...
The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent.Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes.
In a modern context the first organic (carbon–containing) radical identified was the triphenylmethyl radical, (C 6 H 5) 3 C •. This species was discovered by Moses Gomberg in 1900. In 1933 Morris S. Kharasch and Frank Mayo proposed that free radicals were responsible for anti-Markovnikov addition of hydrogen bromide to allyl bromide. [25] [26]
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.