The Reactivity of Nitrile Imines

One of the most unique properties of nitrile imines in comparison to other 1,3-dipoles is their diverse reactivity profile with a number of distinct substrates. This chapter aims to categorise the different transformations of the dipole that have been reported in the literature over the past 60 years. Of particular utility is the conventional 1,3-dipolar cycloaddition reaction between the nitrile imine and unsaturated carbon-carbon bonds. While further research is required to fully comprehend the factors determining the rate and regioselectivity of such reactions, these aspects are also discussed. Nitrile imines also exhibit substantial reactivity with a number of nucleophiles, particularly softer examples such as carboxylic acids and thiols. In the absence of any reaction partners, certain species of nitrile imine are also labile to undergo intramolecular rearrangement, dimerisation, or decomposition.