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A Neutral Three‐Membered 2π Aromatic Disilaborirane and the Unique Conversion into a Four‐Membered BSi2N‐Ring
We report the design, synthesis, structure, bonding, and reaction of a neutral 2π aromatic three‐membered disilaborirane. The disilaborirane is synthesized by a facile one‐pot reductive dehalogenation of amidinato‐silylene chloride and dibromoarylborane with potassium graphite. Despite the tetravale...
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Published in: | Angewandte Chemie International Edition 2020-12, Vol.59 (51), p.23015-23019 |
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Main Authors: | , , , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Online Access: | Get full text |
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Summary: | We report the design, synthesis, structure, bonding, and reaction of a neutral 2π aromatic three‐membered disilaborirane. The disilaborirane is synthesized by a facile one‐pot reductive dehalogenation of amidinato‐silylene chloride and dibromoarylborane with potassium graphite. Despite the tetravalent arrangement of atoms around silicon, the three‐membered silicon‐boron‐silicon ring is aromatic, as evidenced by NMR spectroscopy, nucleus independent chemical shift calculations, first‐principles electronic structure studies using density functional theory (DFT) and natural bond orbital (NBO) based bonding analysis. Trimethylsilylnitrene, generated in situ, inserts in the Si−Si bond of disilaborirane to obtain a four‐membered heterocycle 1‐aza‐2,3‐disila‐4‐boretidine derivative. Both the heterocycles are fully characterized by X‐ray crystallography.
A neutral 2π electronic three‐membered aromatic disilaborirane is reported where aromatic stabilization arises from the overlap of a p orbital on boron and two σ* MOs of silicon. Also, the intriguing reactivity of the disilaborirane is studied and a four‐membered heterocycle is obtained. |
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ISSN: | 1433-7851 1521-3773 |
DOI: | 10.1002/anie.202009638 |