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Alternatively, benzene may react with carbon tetrachloride using the same catalyst to obtain the triphenylmethyl chloride–aluminium chloride adduct which is then treated with diethyl ether for 24 hours at room temperature and hydrolyzed with concentrated hydrochloric acid: [3] 3 C 6 H 6 + CCl 4 + AlCl 3 → Ph 3 CCl·AlCl 3 Ph 3 CCl·AlCl 3 ...
Triphenylmethylsodium can be prepared from trityl chloride dissolved in an aprotic solvent and sodium: [4] (C 6 H 5) 3 CCl + 2 Na → (C 6 H 5) 3 CNa + NaCl. Reaction with silver hexafluorophosphate gives triphenylmethyl hexafluorophosphate. Trityl chloride reacts with zinc in nonpolar solvents (e.g. benzene) to form Gomberg's dimer. [5]
The reagent can be prepared in two steps from triphenylphosphine.The first step is P-alkylation with chloromethyl methyl ether.. PPh 3 + CH 3 OCH 2 Cl → [CH 3 OCH 2 PPh 3]Cl. In the second step, the resulting phosphonium salt is deprotonated.
Trityl (triphenylmethyl, Tr) — Removed by acid [20] [21] [22] and hydrogenolysis; p-Methoxybenzyl ether (PMB) — Removed by acid, hydrogenolysis, or oxidation – commonly with DDQ. [23] p,m‑Dimethoxybenzyl ether — Removed via oxidation with DDQ or ceric ammonium chloride [24] Acetals:
The presence of three adjacent phenyl groups confers special properties manifested in the reactivity of the alcohol. For example it reacts with acetyl chloride, not to give the ester, but triphenylmethyl chloride: [5] Ph 3 COH + MeCOCl → Ph 3 CCl + MeCO 2 H. The three phenyl groups also offer steric protection.
The triphenylmethyl radical can be prepared by homolysis of triphenylmethyl chloride 1 by a metal like silver or zinc in benzene or diethyl ether. The radical 2 forms a chemical equilibrium with the quinoid-type dimer 3 (Gomberg's dimer). In benzene the concentration of the radical is 2%. [3] Triphenylmethyl radical
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 ...
Moses Gomberg (February 8, 1866 – February 12, 1947) was a chemistry professor at the University of Michigan. [1] He was elected to the National Academy of Sciences and the American Philosophical Society, [2] [3] and served as president of the American Chemical Society. [4]