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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.
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:
[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.
C 19 H 17 O 4 P: cresyl diphenylphosphate: 26444-49-5 C 19 H 18 ClN 3 O 3: camazepam: 36104-80-0 C 19 H 18 Si: methyltriphenylsilane: 791-29-7 C 19 H 18 Sn: methyltriphenyltin: 1089-59-4 C 19 H 19 ClFNO 3: flamprop isopropyl: 52756-22-6 C 19 H 19 N: phenindamine: 82-88-2 C 19 H 19 N 7 O 6: folic acid: 59-30-3 C 19 H 20 ClN 3: clemizole: 442-52 ...
[4] Methylenetriphenylphosphorane is used to replace oxygen centres in aldehydes and ketones with a methylene group, i.e., a methylenation: R 2 CO + Ph 3 PCH 2 → R 2 C=CH 2 + Ph 3 PO. The phosphorus-containing product is triphenylphosphine oxide.