Behaviour of nitrile oxides towards nucleophiles. Part IV. Heteromacrocycles from acetonitrile oxide

Abstract

Several polymers of acetonitrile oxide have been obtained by treatment of the pure monomer with pyridine or trimethylamine. Spectroscopic properties of dimer, hexamer, heptamer, and octamer support stereoregular unsaturated monocyclic structures: this has been confirmed, for one of them, by crystallographic analysis. Another polymer, which is the main product from very concentrated solutions of acetonitrile oxide and trimethylamine, is believed to have a linear structure. A polymerization mechanism is suggested.