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).
A credit to donation: A diverse range of electrophilic addition reactions, conventionally carried out using Lewis acid catalysts, have been performed in electrophilic media without acidic reagents. 1,1,1,3,3,3‐Hexafluoro‐2‐propanol (HFIP) acts as an efficient hydrogen‐bond donor and highly polar solvent for a wide range of substrates in reactions with Si‐capped π donors.
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