8,9,10,11-Tetrahydro-7H-7,11-propanonaphtho-[1,8-bc][1,5]diazocine (1) is reversibly oxidised to (2) and (3); spectroscopic data for (2) and (3) suggest that simple two-centre 3- and 2-electron σ-bonds are formed in the oxidation.
R. W. Alder, R. Gill and N. C. Goode, J. Chem. Soc., Chem. Commun., 1976, 973 DOI: 10.1039/C39760000973
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