Characterization of Organic Materials. Part I. The Photo-Fries Rearrangement and Related Reactions of a Representative Model for Aromatic Polyurethanes, Ethyl N-Phenylcarbamate.
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The photo-induced transformation of ethyl N-phenylcarbamate 1 to ethyl o-aminobenzoate 2, ethyl p-aminobenzoate 3, and aniline 4 is 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 3 and 4. Author
- Physical Chemistry
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