Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 13, Pages 2967-2972Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201905356
Keywords
azadiboretidines; B; N-heterocycles; diazadiborinines; diboranes; ring expansion
Categories
Funding
- Julius-Maximilians-Universitat Wurzburg
- Deutsche Forschungsgemeinschaft (DFG)
Ask authors/readers for more resources
Several bis(dimethylamino)-substituted 1,4-diaza-2,3-diborinines (DADBs) were synthesized with variable substituents at the backbone nitrogen atoms. By reaction with HCl or BX3 (X=Br, I), these species were successfully converted into their synthetically more useful halide congeners. The high versatility of the generated B-X bonds in further functionalization reactions at the boron centers was demonstrated by means of salt elimination (MeLi) and commutation (NMe2 DADBs) reactions, thus making the DADB system a general structural motif in diborane(4) chemistry. A total of 18 DADB derivatives were characterized in the solid state by X-ray diffraction, revealing a strong dependence of the heterocyclic bonding parameters from the exocyclic substitution pattern at boron. According to our experiments towards the realization of a Dipp-substituted, sterically encumbered DADB, the mechanism of DADB formation proceeds via a transient four-membered azadiboretidine intermediate that subsequently undergoes ring expansion to afford the six-membered DADB heterocycle.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available