Effect of the Structure of Phase-Transfer Catalyst on the Rate of Alkaline Hydrolysis of N-Benzyloxycarbonylglycine 4-Nitrophenyl Ester in the System Chloroform-Borate Buffer

Autor: Baranova, O., Kosmynin, V., Savelova, V., Shendrik, A., Korotkikh, N., Raenko, G., Popov, A.
Zdroj: Russian Journal of Organic Chemistry; March 2002, Vol. 38 Issue: 3 p378-384, 7p
Abstrakt: Onium salts QZ (Z = Cl, Br) having a lipophilic (Q = R3NR', where R' = C16H33) or readily extractable (into organic phase) cation (Q = Ph4P) exhibit a high catalytic activity in phase-transfer alkaline hydrolysis of N-benzyloxycarbonylglycine 4-nitrophenyl ester in the two-phase system chloroform-borate buffer (pH 10). No catalytic effect is observed in the presence of hydrophilic ammonium salts [Et4NCl, Et3PhCH2NCl, Me2(NH2)+NCH2CH2+N(NH2)Me2·2Br-] and those insoluble in organic solvents [(Me)3+NNH(CH2)2COO-·2H2O, Me2(NH2)+NCH2CO-, Me2(NH2)+N(CH2)3SO3-]. These data suggest extraction mechanism of the process. The activity of lipophilic cation Q is determined mainly by two factors: its extractibility, on the one hand, and the ability to form micelles, on the other.
Databáze: Supplemental Index
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