POLYMERIZATION OF AROMATIC NUCLEI .24. INVESTIGATION OF OLIGOMER AND POLYMER FROM FURAN AND TRICHLOROACETIC-ACID

In the reported experiments, a reinvestigation of the oligomeric and polymeric products obtained from furan and trichloroacetic acid was carried out to establish their structures. Comparison of spectral data with those of authentic materials indicated that the major oligomeric products are IV and V. The ratio of the products IV:V was 1:52. Comparison of the polymeric material with IV and V suggests that V is the primary component of the larger chains. In addition, microanalytical and molecular weight data were obtained. These findings are in disagreement with the structural designation of Wassermann et al. , who proposed the presence of units that possessed aliphatic unsaturation (I), and of Kresta and Livingston, who put forth structure III for the same product. Mechanistic aspects are discussed. A limited study was carried out on insoluble polyfuran which was isolated from the reaction of furan with hydrochloric acid.