Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 38, Pages 13575-13581Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201505115
Keywords
azafullerene; deprotonation; hydro-fullerene; reaction mechanisms; regioselectivity
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Funding
- Graduate School of Molecular Science of the Friedrich-Alexander-Universitat Erlangen-Nurnberg (FAU)
- [SFB 953]
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Azafullerenes are as yet the only synthetically available heterofullerenes. Herein, we present plausible reaction pathways towards pentaaryl azafullerenes, focusing on the reactivity of hydro-azafullerene intermediates and their regiochemistry. The X-ray structure of a -hydro-tetraaryl adduct is presented for the first time. The reactivity of dihydro-azafullerene adducts is demonstrated here through H-abstraction in mass spectrometric experiments. Moreover, hydride abstraction and subsequent hydroxylation is possible, as well as deprotonation followed by alkylation.
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