Abstract
The synthesis and characterization of tricyclic guanidinium salts and their reduced polycyclic trisaminomethane derivatives are described. N-ω-Chloroalkyl bicyclic guanidines (3) readily gave tricyclic guanidinium salt (4) in a neutral medium. Treatment of the compounds 4 with anion exchange resin caused facile ring cleavage to yield various macrocyclic compounds 6-9. The compounds 6-9 reverted to the parent tricyclic guanidinium salts in acidic and basic media as a result of transannular interactions. The guanidinium salts 4 were reduced with sodium borohydride to polycyclic trisaminomethane derivatives (11). The structures of 6-9 and 11 are proposed on the basis of the spectral data.
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