STUDY OF DIMERIZATION AND POLYMERIZATION OF N-ALKYLCYANOACETAMIDES

The solution and bulk dimerization of N-alkylcyanoacetamides has been studied in the presence of bases using H-1 and C-13 NMR, IR spectrosco py and SEC. The influence of catalysts has been investigated. The reac tion proceeds in two steps: (i) formation of an enaminonitrile dimer b y the Thorpe reaction; and (ii) intramolecular cyclization of this dim er to a substituted pyridinone. A reaction mechanism is proposed. The application of this reaction to a difunctional compound, N,N'-dodecame thylene-bis(cyanoacetamide), yielded polymers either in solution or in the bulk. Polymers with (M) over bar(n) approximate to 12 000 were ob tained.