Fast H/D exchange of B,B',B''-tribromoborazine in C6D6 in the presence of aluminum tribromide: first evidence for an electrophilic substitution reaction of borazines in solution

Alexey Y Timoshkin; Igor V Kazakov; Anna S Lisovenko; Michael Bodensteiner; Manfred Scheer

doi:10.1021/ic201240h

Fast H/D exchange of B,B',B''-tribromoborazine in C6D6 in the presence of aluminum tribromide: first evidence for an electrophilic substitution reaction of borazines in solution

Inorg Chem. 2011 Sep 19;50(18):9039-44. doi: 10.1021/ic201240h. Epub 2011 Aug 5.

Authors

Alexey Y Timoshkin¹, Igor V Kazakov, Anna S Lisovenko, Michael Bodensteiner, Manfred Scheer

Affiliation

¹ Inorganic Chemistry Group, Department of Chemistry, Saint Petersburg State University, University Pr. 26, Old Peterhof, 198504, Russia. alextim@AT11692.spb.edu

PMID: 21819037
DOI: 10.1021/ic201240h

Abstract

A solution of B,B',B''-tribromoborazine (BrBNH)(3) in excess C(6)D(6) in a sealed NMR tube shows no changes for over 14 months at room temperature but undergoes fast (within minutes) H/D exchange in the presence of AlBr(3) as a Lewis acid, as evidenced by (1)H, (2)H, (11)B, and (27)Al NMR spectroscopy. The proposed electrophilic exchange mechanism is in agreement with the results of DFT computations. To our knowledge, this is the first example of the electrophilic substitution reaction of borazines in solution.