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Transformations involving the pyrrolidine ring of nicotine



Transformations involving the pyrrolidine ring of nicotine



Journal of the Chemical Society Perkin Transactions I (2): 579-585



Nicotine [from Nicotiana tabacum] was oxidized 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 recyclized 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. [Nicotine may be useful as a starting material to convert it into derivatives which might possess useful insecticidal (or other biological or medicinal) properties.].

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Accession: 006826658

Download citation: RISBibTeXText

DOI: 10.1039/p19800000579


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