Single and Multiple Additions of Dibenzoylmethane onto Buckminsterfullerene

A novel dibenzoylmethane‐fullerene e,e,e‐tris adduct was synthesized by the application of a variation of the Bingel–Hirsch conditions and characterized among others by X‐ray crystallography. In addition, the corresponding hexakis adduct was detected by MALDI‐TOF‐MS analysis. Its existence was suppo...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:European journal of organic chemistry 2013-12, Vol.2013 (35), p.7907-7913
Hauptverfasser: Giovannitti, Alexander, Seifermann, Stefan M., Bihlmeier, Angela, Muller, Thierry, Topic, Filip, Rissanen, Kari, Nieger, Martin, Klopper, Wim, Bräse, Stefan
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:A novel dibenzoylmethane‐fullerene e,e,e‐tris adduct was synthesized by the application of a variation of the Bingel–Hirsch conditions and characterized among others by X‐ray crystallography. In addition, the corresponding hexakis adduct was detected by MALDI‐TOF‐MS analysis. Its existence was supported by density‐functional‐theory (DFT) computations. Furthermore a new synthesis of bis(benzoyl)methanofullerene was established, and its molecular structure was elucidated by X‐ray crystallography. DFT computations reproduced the experimentally determined conformation and predict a low energy barrier for the rotation of the two benzoyl moieties. We report the synthesis and crystal structure of tris‐e,e,e‐[bis(benzoyl)methano]fullerene. Furthermore, a new synthetic route to the corresponding mono adduct was developed, and its molecular structure was determined. The corresponding hexakis adduct was predicted by DFT calculations and identified by MALDI‐TOF‐MS as well as by 1H NMR spectroscopy.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201301146