Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Photochemical Rearrangement of 2-Nitrophenyl Phenyl Sulfoxide to 2-Nitrosophenyl Phenyl Sulfone
Rikuhei TanikagaAritsune Kaji
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1973 Volume 46 Issue 12 Pages 3814-3817

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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.

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