Further studies on the chemistry and structure of n-oxides of sparteine and its derivatives—V: Synthesis and structure of 2-phenylsparteine-n16-oxide,a new case of “sponge” proton |
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Authors: | W?adys?aw Boczoń Genowefa Pieczonka Maciej Wiewiórowski |
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Institution: | Institute of Chemistry, Department of Organic Stereochemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland |
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Abstract: | The synthesis of 2-phenylsparteine-N16-oxide (7) and its perchlorate salt (7-H+) was carried out. On the basis of spectral data, and by comparison with appropriate sparteine-N-oxides, the mechanism of formation and the structures of the two new compounds were proposed. It was found, the basicity of the new N-oxide is unexpectedly high and comparable to the basicity of quaternary ammonium hydroxides. The structure and the strength of intramolecular H-bond in 7-H+ makes 7 an excellent “catcher” proton or specific ”sponge” proton. |
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