Photochemical transformations. Part VI. The photorearrangement of 2-nitrofuran and 2-nitropyrrole

Abstract

2-Nitrofuran and 2-nitropyrrole are converted on irradiation into the previously unknown 3-hydroxyiminofuran-2(3H)-one and 3-hydroxyiminopyrrol-2(3H)-one by a process analogous to that reported for the photorearrangement of certain conjugated nitroalkenes. 2-Methyl-5-nitrofuran undergoes an identical rearrangement, whereas 3-methyl-2-nitrofuran is converted into 5-hydroxyimino-3-methylfuran-2(4H)-one.