Nucleophilicity Parameters for Alkyl and Aryl Isocyanides

Nucleophilicity Parameters for Alkyl and Aryl Isocyanides

How nucleophilic are isocyanides? The kinetics of the reactions of alkyl and aryl isocyanides with benzhydrylium ions indicate that isocyanides are 10 orders of magnitude less reactive than the cyanide ion and their nucleophilic reactivity is comparable to that of allylsilanes and silyl enol ethers...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie International Edition 2007-05, Vol.46 (19), p.3563-3566
Hauptverfasser: Tumanov, Vasily V., Tishkov, Alexander A., Mayr, Herbert
Format: Artikel
Sprache:eng
Schlagworte:
carbocations
isocyanides
kinetics
nitrilium ions
reactivity
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:How nucleophilic are isocyanides? The kinetics of the reactions of alkyl and aryl isocyanides with benzhydrylium ions indicate that isocyanides are 10 orders of magnitude less reactive than the cyanide ion and their nucleophilic reactivity is comparable to that of allylsilanes and silyl enol ethers (see the diagram for a comparison of the nucleophilicity N of various isocyanides; Ts=toluene‐4‐sulfonyl).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200605205