Issue 9, 2017

Synthesis of dibromo- and tetrabromo-bipyrrolines and their corresponding 2,6-diazasemibullvalene derivatives

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.

Graphical abstract: Synthesis of dibromo- and tetrabromo-bipyrrolines and their corresponding 2,6-diazasemibullvalene derivatives

Supplementary files

Article information

Article type
Research Article
Submitted
12 Apr 2017
Accepted
08 Jun 2017
First published
12 Jun 2017

Org. Chem. Front., 2017,4, 1785-1788

Synthesis of dibromo- and tetrabromo-bipyrrolines and their corresponding 2,6-diazasemibullvalene derivatives

Z. Huang, M. Zhan, S. Zhang, Q. Luo, W. Zhang and Z. Xi, Org. Chem. Front., 2017, 4, 1785 DOI: 10.1039/C7QO00287D

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