Nucleophilicity Parameters for Alkyl and Aryl Isocyanides

Abstract

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). Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z605205_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.