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Published on: March 25, 2017
A Straightforward Synthetic Route to Monocyclic 1,3,2,4-Diazadiborinines
Xin Yue1, Linlin Wu2, Hao Wang1,3
1School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P. R. China.
Abstract:
A novel straightforward synthetic route to monocyclic 1,3,2,4-diazadiborinines has been developed by the sequential reaction of the NHC-coordinated iminoborane with bases and haloboranes (or borate). The first examples of monocyclic 1,3,2,4-diazadiborinines featuring different functional groups on the two B atoms have been synthesized and structurally characterized. Further derivatization of 4-bromophenyl-substituted 1,3,2,4-diazadiborinine has also been achieved, giving the biphenyl-substituted 1,3,2,4-diazadiborinine. The aromaticity of these newly synthesized 1,3,2,4-diazadiborinines was also studied by theoretical calculations.
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Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

