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Synthesis of α,α,α′,α′-Tetrachloro‑Δ1‑bipyrrolines and 4,8-Dichloro-2,6-diazasemibuvallenes

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journal contribution
posted on 2015-02-20, 00:00 authored by Ming Zhan, Shaoguang Zhang, Zhe Huang, Zhenfeng Xi
A series of 4,8-dichloro-2,6-diazasemibullvalenes were synthesized and isolated from the reaction of α,α,α′,α′-tetrachloro-Δ1-bipyrrolines with lithium via C–N bond formation. All those dichlorodiazasemibullvalene derivatives demonstrated extremely rapid aza-Cope rearrangement in solution. An unprecedented skeletal rearrangement of 4,8-dichloro-2,6-diazasemibullvalene derivatives took place, resulting in the formation of a new bipyrroline skeleton.