Evidence of a borderline region between E1cb and E2 elimination reaction mechanisms: a combined experimental and theoretical study of systems activated by the …

…, F De Angelis, L Ottavi, M Papavasileiou…

Index: Alunni, Sergio; De Angelis, Filippo; Ottavi, Laura; Papavasileiou, Magdalini; Tarantelli, Francesco Journal of the American Chemical Society, 2005 , vol. 127, # 43 p. 15151 - 15160

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Citation Number: 35

Abstract

We report a combined experimental and theoretical study to characterize the mechanism of base-induced β-elimination reactions in systems activated by the pyridyl ring, with halogen leaving groups. The systems investigated represent borderline cases, where it is uncertain whether the reaction proceeds via a carbanion intermediate (E1cb, AxhDH+ DN) or via the concerted loss of a proton and the halide (E2, ANDEDN) upon base attack. Experimentally ...

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