Synthesis of Highly Reactive Polymer Nitrile <i>N</i>‑Oxides for Effective Solvent-Free Grafting

Abstract

A one-pot synthesis of polymer nitrile <i>N</i>-oxides was achieved via the Michael addition of living polymer anions derived from vinyl monomers to commercially available <i>trans</i>-β-nitrostyrene and subsequent dehydration with concd H₂SO₄. The polymer nitrile <i>N</i>-oxides are effective as grafting agents in catalyst- and solvent-free 1,3-dipolar cycloadditions to unsaturated-bond-containing polymers with high conversion and exhibit higher reactivity compared to that of nitrile <i>N</i>-oxides prepared from 1,1-diphenylnitroethene. Application to the preparation of a functional glass surface was demonstrated using P<i>t</i>BMA nitrile <i>N</i>-oxide as a grafting agent