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Photochemical Rearrangement of 2-Nitrophenyl Phenyl Sulfoxide to 2-Nitrosophenyl Phenyl Sulfone

1973; Oxford University Press; Volume: 46; Issue: 12 Linguagem: Inglês

10.1246/bcsj.46.3814

1348-0634

Rikuhei Tanikaga, Aritsune Kaji,

Chemistry and Chemical Engineering

Abstract Irradiation of 2-nitrophenyl phenyl sulfoxide (I) gave 2-nitrosophenyl phenyl sulfone (II) as the sole product. The rearrangement was not affected by a quencher, but took a different course in the presence of a sensitizer or a halogen-containing solvent. When I with an electron-donating substituent at a 4′-position or electron-withdrawing one at a 4-position was irradiated, the corresponding II was obtained in a lower yield. 2-Nitrophenyl phenyl sulfide was photochemically stable. From the results, it is proposed that in the excited singlet state of I the oxyanion of a nitro group attacks the positive sulfur atom, and oxygen transfer takes place.