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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]
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 ...
[4] 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
C 19 H 17 ClN 2 O 4: glafenine: 3820-67-5 C 19 H 17 ClN 2 O 4: quizalofop ethyl: 76578-14-8 C 19 H 17 N: tritylamine: 5824-40-8 C 19 H 17 NOS: tolnaftate: 2398-96-1 C 19 H 17 NO 2: naproanilide: 51888-81-4 C 19 H 17 NO 2: neocinchophen: 485-34-7 C 19 H 17 N 3: triphenyl guanidine: 603-53-2 C 19 H 17 O 4 P: cresyl diphenylphosphate: 26444-49-5 C ...
It is the thiol derivative of the bulky substituent triphenylmethyl (called trityl). [1] [2] The compound forms a number of unusual derivatives that are more stable than less bulky analogues. The sulfenyl chloride (C 6 H 5) 3 CSCl is obtained from the thiol with sulfuryl chloride. It in turn reacts with ammonia to form the sulfenamide (C 6 H 5 ...
This reaction can be optimized by carefully controlling the amount of organolithium reagent addition, or using trimethylsilyl chloride to quench excess lithium reagent. [40] A more common way to synthesize ketones is through the addition of organolithium reagents to Weinreb amides (N-methoxy-N-methyl amides).
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