Tuning the Reducing Properties of 1,2-Diaryl-1,2-disodiumethanes

We investigated the reducing properties of a series of 1,2-diaryl-1,2-disodiumethanes by means of equilibration reactions. The electron-donor power of these vic-diorganometals is strongly affected by the nature of substituents present either on the aromatic ring(s) or on the carbanionic centers, and...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2009-11, Vol.74 (21), p.8064-8070
Hauptverfasser: Azzena, Ugo, Pisano, Luisa, Antonello, Sabrina, Maran, Flavio
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:We investigated the reducing properties of a series of 1,2-diaryl-1,2-disodiumethanes by means of equilibration reactions. The electron-donor power of these vic-diorganometals is strongly affected by the nature of substituents present either on the aromatic ring(s) or on the carbanionic centers, and it can be correlated with their ability to delocalize the arylmethyl carbanions. These findings are supported by electrochemical analysis of the reduction behavior of the parent 1,2-diarylalkene. Applications of these results to the reduction of selected substrates are described.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo901183x