Isocyanide - Reactions

Reactions

Isocyanides are stable to strong base (they are often made under strongly basic conditions), but they are sensitive to acid. In the presence of aqueous acid, isocyanides hydrolyse to the corresponding formamides. However, some isocyanides can polymerize in the presence of acids. Acid hydrolysis is a convenient method for removing the obnoxiously odoriferous isocyanides.

Isocyanides are reactants in many multicomponent reactions of interest in organic synthesis, two of which are: the Ugi reaction and the Passerini reaction.

Isocyanides participate in cycloaddition reactions, such as the cycloaddition with tetrazines. Depending on the degree of substitution of the isocyanide, this reaction converts isocyanides into carbonyls or gives stable cycloadducts.

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