Mechanism and proton activating factors in base-induced β-elimination reactions of N-[2-(4-pyridyl)ethyl]quinuclidinium and N-[2-(2-pyridyl)ethyl]quinuclidinium salts

Sergio Alunni; Annarita Conti; Rosa Palmizio Errico

doi:10.1039/A908881D

Mechanism and proton activating factors in base-induced β-elimination reactions of N-[2-(4-pyridyl)ethyl]quinuclidinium and N-[2-(2-pyridyl)ethyl]quinuclidinium salts

Sergio Alunni,*^a Annarita Conti^a and Rosa Palmizio Errico^a

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^a Dipartimento di Chimica, Università di Perugia, Perugia, Italy

Abstract

β-Elimination reactions of N-[2-(4-pyridyl)ethyl]quinuclidinium and N-[2-(2-pyridyl)ethyl]quinuclidinium salts (N) in acetohydroxamate–acetohydroxamic acid buffer, H₂O, μ = 1 M KCl, 50 °C, with the formation of 4- or 2-vinylpyridine, respectively, proceed by an E1cb mechanism with carbon deprotonation occurring in the substrates protonated at the pyridine ring (NH⁺). The formation of the intermediate carbanion has a high degree of reversibility. The systems consistently present H/D exchange. NH⁺ is much more reactive than N; this can be attributed to the strong stabilization of the intermediate carbanion formed from NH⁺ due to resonance.

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The article was received on 08 Nov 1999, accepted on 17 Jan 2000 and first published on 21 Feb 2000

Article type: Paper

DOI: 10.1039/A908881D

Citation: J. Chem. Soc., Perkin Trans. 2, 2000,0, 453-457

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Mechanism and proton activating factors in base-induced β-elimination reactions of N-[2-(4-pyridyl)ethyl]quinuclidinium and N-[2-(2-pyridyl)ethyl]quinuclidinium salts

S. Alunni, A. Conti and R. Palmizio Errico, J. Chem. Soc., Perkin Trans. 2, 2000, 0, 453
DOI: 10.1039/A908881D
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Journal of the Chemical Society, Perkin Transactions 2

Mechanism and proton activating factors in base-induced β-elimination reactions of N-[2-(4-pyridyl)ethyl]quinuclidinium and N-[2-(2-pyridyl)ethyl]quinuclidinium salts

Abstract

Supplementary files

Publication details

Mechanism and proton activating factors in base-induced β-elimination reactions of N-[2-(4-pyridyl)ethyl]quinuclidinium and N-[2-(2-pyridyl)ethyl]quinuclidinium salts

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