Catalytic cracking of organic amides: II. Use of substituted amides, mechanism, and a predictive index for reactivity

Abstract

Previously we described catalysts for the efficient cracking of ethylidene bis formamide to N-vinyl formamide. Surprisingly, non-acidic catalysts operate at lower temperatures than described earlier for less selective catalysts. This manuscript describes the extension of the catalytic technology to other amides. Data for a variety of different substituted amides is used to propose a mechanism for this cracking reaction. In addition a “vinyl cracking index” is proposed (based upon the relative conversion of an acetal vs. an ether over the same catalyst) which allows us to rank current catalysts and forecast new catalysts for the cracking of N-vinyl amides precursors.