Photoinduced rearrangement of α-(2-nitrophenyl)ketones

Photoirradiation of alpha-(2-nitrophenyl)ketones produced cyclic hydroxamates. The reaction proceeded via photoinduced oxygen transfer from the nitro group to the benzylic position, forming an alpha-hydroxyketone having a nitroso group. Subsequent addition of the nitroso group to the ketone moiety and the concomitant cleavage of the C-C sigma bond between the carbonyl group and the benzyl position produced hydroxamic acid, which underwent formation of a hemiacetal to give cyclic hydroxamate.

Automated summary

In this study, photoirradiation of alpha-(2-nitrophenyl)ketones resulted in the production of cyclic hydroxamates. The reaction involved photoinduced oxygen transfer from the nitro group to the benzylic position, leading to the formation of an alpha-hydroxyketone with a nitroso group. Subsequent addition of the nitroso group to the ketone moiety and the cleavage of the C-C sigma bond between the carbonyl group and the benzyl position produced hydroxamic acid, which then underwent hemiacetal formation to yield cyclic hydroxamate.