Photoinduced rearrangement of α-(2-nitrophenyl)ketones. Issue 40 (30th September 2022)

• Record Type: Journal Article
• Authors: Kitayama, Shinnosuke; Shimizu, Hiroaki; Yokoshima, Satoshi
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 40(2022)
• Page Start: 7896
• Page End: 7899
• Publication Date: 2022-09-30
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01546c
• Languages: English
• ISSNs: 1477-0520

Abstract

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