Efficient synthesis of aza-triquinacene derivatives via cycloaddition of 2,6-diazasemibullvalenes with nitroso compounds.

The reaction between 2,6-diazasemibullvalenes and nitroso compounds was investigated. Aza-triquinacene derivatives of interesting structural and synthetic chemistry were generated highly selectively in good to excellent isolated yields. This reaction, which was rarely found between common aziridine derivatives and nitroso compounds, could be attributed to the rigid polycyclic ring system and the substitution patterns of 2,6-diazasemibullvalenes. Δ(1) -Bipyrroline derivatives were formed in excellent yields when these aza-triquinacene derivatives were treated with SmI2 .