Investigating the ring expansion reaction of pentaphenylborole and an azide
| Autor: | Jason L. Dutton, Trevor K. Thompson, David J. D. Wilson, Caleb D. Martin, Shannon A. Couchman |
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| Rok vydání: | 2014 |
| Předmět: |
Bicyclic molecule
Stereochemistry Metals and Alloys General Chemistry Ring (chemistry) Medicinal chemistry Catalysis Surfaces Coatings and Films Electronic Optical and Magnetic Materials Adduct Cyclooctatetraene chemistry.chemical_compound chemistry Trimethylsilyl azide Materials Chemistry Ceramics and Composites Azide Borole |
| Zdroj: | Chem. Commun.. 50:11724-11726 |
| ISSN: | 1364-548X 1359-7345 |
| DOI: | 10.1039/c4cc04864d |
| Popis: | The reaction between trimethylsilyl azide and pentaphenylborole was recently shown to produce the corresponding 1,2-azaborine. Investigating this transformation theoretically suggests that the reaction proceeds via coordination of the azide to the borole, rearrangement to a bicyclic species, and conversion to a kinetically favoured eight-membered BN3C4 heterocycle or expulsion of N2 to furnish the thermodynamically favoured 1,2-azaborine. The eight-membered species was structurally characterized as a borole adduct and represents an unusual analogue of cyclooctatetraene. |
| Databáze: | OpenAIRE |
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