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Communication | Regular issue | Vol 63, No. 2, 2004, pp.241-247
Published online, 15th December, 2003
DOI: 10.3987/COM-03-9942
Selective Phototransformation of Hydroxy-substituted Aromatic Nitrones into N,N-Diarylformamide Derivatives Showing a Novel Conformational Isomerism

Harunobu Kondo, Kenta Tanaka , Kanji Kubo, Tetsutaro Igarashi, and Tadamitsu Sakurai*

*Departmnet of Applied Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan

Abstract

On irradiation in acetonitrile at 366 nm, photorearrangements of the title aromatic nitrones (1) proceeded to give selectively N,N-diarylformamides, which showed a novel conformational isomerism without undergoing large substituent, solvent, and temperature effects. An analysis of substituent and solvent effects on the product distribution confirmed that a hydrogen-bonding interaction with the ring nitrogen in oxaziridine intermediates plays a crucial role in inducing the selective transformation of 1 into the corresponding formamide derivatives.