Polymer synthesis exploiting nitrile N-oxide

Abstract

Highly sophisticated supramolecular and macromolecular multi-component architectures strongly require viable means of powerful, versatile, and reliable synthetic routes. For this purpose, nitrile N-oxide is potentially useful as a 'molecular glue' between functional components because nitrile N-oxide allows catalyst-free reactions with various unsaturated bonds, along with a rigid C-C bond formation. However, there are only a few reports concerning applications of nitrile N-oxides toward a chemical modification and a chemical ligation, probably due to the extreme reactivity of nitrile N-oxides leading to spontaneous dimerization to give a furoxan. This paper summarizes the reports of polymer synthesis exploiting nitrile N-oxides. Through the historical survey, the efficiency and application of our recently developed method of polymer synthesis, based on the kinetic stabilization of nitrile N-oxides, are discussed in detail. © 2011, The Society of Polymer Science, Japan.