Oxidation of piperidines, pyrrolidine, azetidine, perhydroazepine, and perhydroazocine with aqueous alkaline sodium peroxodisulphate in the presence of silver nitrate gave 1,1′-bipiperidines, a trimer of 1-pyrroline,1,1′-biazetidine,1,1′-biperhydroazepine together with 1-formylperhydroazepine, and 1-formylperhydroazocine, respectively.
K. Ogawa, Y. Nomura, Y. Takeuchi and S. Tomoda, J. Chem. Soc., Perkin Trans. 1, 1982, 3031 DOI: 10.1039/P19820003031
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