Stabilization of the Elusive 9‐Carbene‐9‐Borafluorene Monoanion
Citations Over TimeTop 23% of 2021 papers
Abstract
Abstract Two‐electron reduction of carbene‐supported 9‐bromo‐9‐borafluorenes with excess KC 8 , Na, or Li‐naphthalenide affords six N‐heterocyclic carbene (NHC)‐ or cyclic(alkyl)(amino) carbene (CAAC)‐stabilized borafluorene anions ( 3 – 8 )‐the first isolated and structurally authenticated examples of the elusive 9‐carbene‐9‐borafluorene monoanion. The electronic structure, bonding, and aromaticity of the boracyclic anions were comprehensively investigated via computational studies. Compounds 5 and 8 react with metal halides via salt elimination to give new B‐E (E=Au, Se, Ge)‐containing materials ( 9 – 12 ). Upon reaction with diketones, the carbene ligand cleanly dissociates from 5 or 8 to yield new B‐O containing spirocycles ( 13 – 14 ) that cannot be easily obtained using “normal” valent borafluorene compounds. Collectively, these results support the notion that carbene‐stabilized monoanionic borafluorenes may serve as a new platform for the one‐step construction of higher‐value boracyclic materials.
Related Papers
- → Halogen exchange reactions between alkyl halides and aqueous hydrogen halides. A new method for preparation of alkyl halides.(1990)29 cited
- → Reaction of alkyl halides with dialkyltins(1967)12 cited
- → Reaction of 2-cyanomethylbenzimidazole with alkyl halides(1988)5 cited
- → Symmetrical and Unsymmetrical Coupling of Alkyl Halides Mediated by Grignard Reaction(1989)5 cited
- → The Use of S-Alkyl-N-Phenylthiuronium Picrates, Styphnates and Picrolonates for the Characterisation of Alkyl Halides(1960)2 cited