title: Hydro-aza-(C59 N)fullerenes: Formation Mechanism and Hydrogen Substitution.
abstract: 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 β'-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.
authors.affiliation: Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Regina
authors.initials: R
authors.lastname: Eigler
authors.affiliation: Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Egerlandstrasse 1, 91058, Erlangen, Germany.
authors.forename: Frank W
authors.initials: FW
authors.lastname: Heinemann
authors.affiliation: Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Henkestrasse 42, 91054, Erlangen, Germany. andreas.hirsch@fau.de.
authors.forename: Andreas
authors.identifier: http://orcid.org/0000-0003-1458-8872
authors.initials: A
authors.lastname: Hirsch
keywords: azafullerene; deprotonation; hydro-fullerene; reaction mechanisms; regioselectivity