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Treatment of Δ1-dipyrrolines with NBS afforded α,α′-dibromo-Δ1-bipyrrolines and α,α,α′,α′-tetrabromo-Δ1-bipyrrolines respectively with excellent selectivity depending on the amount of NBS. All these multibromo-substituted Δ1-bipyrrolines could be efficiently transformed into their corresponding… Click to show full abstract
Treatment of Δ1-dipyrrolines with NBS afforded α,α′-dibromo-Δ1-bipyrrolines and α,α,α′,α′-tetrabromo-Δ1-bipyrrolines respectively with excellent selectivity depending on the amount of NBS. All these multibromo-substituted Δ1-bipyrrolines could be efficiently transformed into their corresponding 2,6-diazasemibullvalene derivatives via reduction with lithium. An unprecedented rearrangement of 4,8-dibromo-2,6-diazasemibullvalene afforded a new type of bipyrroline derivative.
Journal Title: Organic chemistry frontiers
Year Published: 2017
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