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- Title
Isomer Dependence on the Reactivity of Diazenes with Pentaphenylborole.
- Authors
Adiraju, Venkata A. K.; Martin, Caleb D.
- Abstract
Reactions of the anti-aromatic pentaphenylborole with diazenes indicate that both the substitution and the isomer influence the reaction outcome. With respect to trans isomers, azobenzene underwent coordination and C−H addition across the diene of the borole, and 2′,6′-dimethylazobenzene furnished a fused tricyclic system. Under photolytic conditions, both of the aforementioned diazenes generate the first 1,3,2-diazaborepin heterocycles, rationalized through reactivity with the cis isomers. This notion is corroborated by the reaction of pentaphenylborole with benzo[ c]cinnoline, the tethered variant of azobenzene, that only exists as the cis conformer as the corresponding 1,3,2-diazaborepin was produced regardless if the reaction is conducted in the dark or light. The more aromatic pyridazine proved to be less reactive, forming a resilient adduct.
- Subjects
DIAZENES; IMIDES; CHEMICAL reactions; ISOMERS; PYRIDAZINES
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 47, p11437
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201702539