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Issue 0, 1980
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Transformations involving the pyrrolidine ring of nicotine

Abstract

Nicotine was oxidised to cotinine and this successively alkylated and reduced to a series of 4′-mono- and 4′,4′-di-alkylnicotines, the mass spectra of which are discussed. The pyrrolidine ring has been opened with ethyl chloroformate and the product both recyclised to S-nicotine without loss of optical activity and converted to metanicotine. The dihydrochloride of the last, on successive treatment with bromine and sodium hydrogencarbonate, yielded 3′-bromonicotine. Cotinine has been converted into various derivatives, and the demethylation of nicotine has been investigated.

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Article type: Paper
DOI: 10.1039/P19800000579
J. Chem. Soc., Perkin Trans. 1, 1980, 579-585

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    Transformations involving the pyrrolidine ring of nicotine

    R. M. Acheson, M. J. Ferris and N. M. Sinclair, J. Chem. Soc., Perkin Trans. 1, 1980, 579
    DOI: 10.1039/P19800000579

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