Abstract
The salts and quaternary derivatives of 2-methylene-3-hydroxyquinuclidine readily add nucleophilic reagents because of the high polarity and polarizability of the carbon-carbon double bond, which are due to the overall electron-acceptor effect of the positively charged nitrogen atom and the carbonyl group. The double bond is substantially deactivated in the base, and the addition of nucleophilic reagents is hindered.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1370–1376, October, 1977.
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Vorob'eva, V.Y., Bondarenko, V.A., Mikhlina, E.E. et al. Reaction of 2-methylene-3-oxoquinuclidine with nucleophilic reagents. Chem Heterocycl Compd 13, 1098–1104 (1977). https://doi.org/10.1007/BF00480146
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DOI: https://doi.org/10.1007/BF00480146