Polymerization behavior of N-phenylbenzoxazine in bulk was studies in detail to discover new reaction pathways: (1) formation of an intermediary polymer having N,O-acetal-type linkage in the main chain and (2) its rearrangement into Mannich-type linkage in the solid state. Efficient promotion of the main chain rearrangement was achieved by using a dual system composed of imidazole and sulfonic acid.

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Abstract1,3‐Benzoxazine monomers having ammonium salt of carboxylic acid have been developed. These 1,3‐benzoxazines 1a and 1b were easily synthesized from the corresponding tetrabutylammonium salts of glycine and β‐alanine, respectively. The glycine‐derived benzoxazine 1a exhibited remarkably high reactivity, which allowed its thermally induced ring‐opening polymerization in bulk at 100 °C, at which N‐methyl‐1,3‐benzoxazine 1d did not undergo the polymerization at all. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

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