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Reactivity and Mechanism of 1-X-2-(O-Nitrophenyl)Ethanes in Base Induced β-Elimination Reactions With Formation of O-Nitrostyrene

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Studies of acid-base catalysis in acetohydroxamic/acetohydroxamate buffers, H/D exchange and solvent isotope effect show that the mechanism of the β-elimination with the formation of o-nitrostyrene from the N-[2-(o-Nitrophenyl)ethyl] quinuclidinium ion (1) is E1cb, 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 °C in OH-/H2O, μ = 1 M KCl, the second order rate constant for the elimination reaction from (1) is kOH = 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] (kOH = 0.77 .10-3 M-1 s-1).

Affiliations: 1: Dipartimento di Chimica, Università di Perugia, 06100 - Perugia, Italy; 2: Dipartimento di Chimica, Università di Potenza, 85100 - Potenza, Italy


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