Craig Jamieson - The Nitrile Imine 1,3-Dipole: Properties, Reactivity and Applications

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The authors dedicate this work to Rolf Huisgen and his many coworkers, the architects of a tremendous portion of the 1,3-dipole chemistry in use today.

We also wish to clarify a handful of technical details relating to the construction of this manuscript. Firstly, all reported products of 1,3-dipolar cycloaddition reactions afford a single or extremely dominant regioisomer unless otherwise indicated.

Additionally, the literature concerning NIs is dominated by 1,3-dipolar cycloadditions with alkenes, and this may appear disproportionate relative to the page allocation for different NI reaction partners within theReactivitysection of this book. We have taken this decision for two reasons. Firstly, the majority of examples of NI-alkene cycloadditions not reported herein apply this reaction as a means to an end and is not the primary focus of the manuscript. All relevant articles that in some manner further the understanding of, or expand the application scope of, the NI-alkene cycloaddition have been included within this book, along with other selected examples. Secondly, the principal objective of theReactivitysection of this work is to provide a complete and balanced overview of all potential reaction partners. A vast excess of NI-alkene cycloaddition methodology would only dilute the impact and compromise the structuring of this section.

This book is intended to provide complete, authoritative coverage of the literature up to May 2019 (inclusive). While a handful of citations after this date are included, the authors must stress that it is possible that some publications after this time may have been overlooked due to the preparation of the manuscript taking place during this period.

The generation of nitrile imines (NIs) can be traced back to the beginning of the twentieth century, although these reports lacked both characterisation and application of the highly reactive species. The first synthetically tractable report came from Huisgen in 1959 [].

Interest in the applications of NIs was more sparse over the next few decades, with the majority of publications focussing instead on the mechanism of their formation, or their reactivity with different substrates. Recently, however, NI chemistry has enjoyed a renaissance throughout the literature, with a raft of applications identified in the synthesis of APIs, bioorthogonal conjugation, and materials chemistry, over the past fifteen years [].