Characterization of Organic Materials. Part I. The Photo-Fries Rearrangement and Related Reactions of a Representative Model for Aromatic Polyurethanes,Ethyl N-Phenylcarbamate.

摘要

The photo-induced transformation of ethyl N-phenylcarbamate 1to ethyl o-aminobenzoate 2,ethyl p-aminobenzoate 3,and aniline 4is concentration dependent. At low concentrations,aniline is the exclusive non-polymeric product. At higher concentrations of 1,all three products are observed with 2 predeominating but the photo-yield is reduced. The results are interpreted in terms of hydrogen-bonded aggregations at higher concentrations which favors photo-Fries reaction and the photo-lability of 3and 4. (Author)