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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 ...
The alkylphosphonium salt is deprotonated with a strong base such as n-butyllithium: [Ph 3 P + CH 2 R]X − + C 4 H 9 Li → Ph 3 P=CHR + LiX + C 4 H 10. Besides n-butyllithium (n BuLi), other strong bases like sodium and potassium t-butoxide (t BuONa, t BuOK), lithium, sodium and potassium hexamethyldisilazide (LiHMDS, NaHMDS, KHDMS, where HDMS = N(SiMe 3) 2), or sodium hydride (NaH) are also ...
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.
[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
Crystallographic characterization of the colourless ylide reveals that the phosphorus atom is approximately tetrahedral. The PCH 2 centre is planar and the P=CH 2 distance is 1.661 Å, which is much shorter than the P-Ph distances (1.823 Å). [5] The compound is usually described as a combination of two resonance structures: Ph 3 P + CH 2 − ...
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. It is well miscible in diethyl ether and benzene, but it is practically insoluble in water, and partially in ethanol.