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). (Chemical Equation Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
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Tumanov, V. V., Tishkov, A. A., & Mayr, H. (2007). Nucleophilicity parameters for alkyl and aryl isocyanides. Angewandte Chemie - International Edition, 46(19), 3563–3566. https://doi.org/10.1002/anie.200605205
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