Reactivity and mechanism of 1-X-2-(O-nitrophenyl)ethanes in base induced β-elimination reactions with formation of O-nitrostyrene

被引：8

作者：

Alunni, S

Ruzziconi, R

Teofrasti, O

机构：

[1] Univ Perugia, Dipartimento Chim, I-06100 Perugia, Italy

[2] Univ Potenza, Dipartimento Chim, I-85100 Potenza, Italy

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 1999年 / 25卷 / 05期

关键词：

D O I：

10.1163/156856799X00077

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Studies of acid-base catalysis in acetohydraxamic/acetohydroxamate buffers, WD exchange and solvent isotope effect show that the mechanism of the beta-elimination with the formation of o-nitrostyrene from the N-[2-(o-Nitrophenyl)ethyl] quinuclidinium ion (1) is E(1)cb, involving an intermediate carbanion formed with a high degree of reversibility. The reactivity of 1-X-2-o-nitrophenylethanes with various leaving groups such Br, Cl, F, quinuclidine, and tetrahydrothiophene in OH./H2O is reported. At 25 degrees C in OH-/H2O, mu = 1 M KCl, the second order rate constant for the elimination reaction from (1) is k(OH) = 4.9 . 10(-5) M-1 s(-1) and it is 15.7 times lower than that of the corresponding p-nitro substituted analogue [1] (k(OH) = 0.77 . 10(-3) M-1 s(-1)).

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页码：483 / 495

页数：13

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