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Title
Japanese: 
English:Photoreaction of nitrobenzene derivatives with alkyl thiols giving sulfonamides and derivatives 
Author
Japanese: 湯浅英哉, 遊部智大, 金森功吏.  
English: HIDEYA YUASA, Tomohiro Yube, Takashi Kanamori.  
Language English 
Journal/Book name
Japanese: 
English:Phosphorus Sulfur Silicon Relat. Elem. 
Volume, Number, Page        
Published date Apr. 8, 2023 
Publisher
Japanese: 
English: 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
DOI https://doi.org/10.1080/10426507.2023.2195651
Abstract Here, we serendipitously found that photoirradiation of nitrobenzene derivatives with alkyl thiols produced sulfonamides in low yields without the addition of other reagents. We proposed a new photoreaction mechanism, in which the photo-excited nitrobenzene biradical abstracts a hydrogen atom from H-S, the resultant thiyl radical undergoes the coupling with the nitrogen atom in the nitro group, and the two oxygen atoms in the nitro group are transferred onto the sulfur atom. The photoreaction by-produced p-sulfanyl, aniline, and o-sulfonyl derivatives presumably through SRN1 mechanism from the p-substituted nitrobenzene, photo-desulfonylation, and photo-Fries rearrangement from the sulfonamide, respectively. Discovery of this photoreaction will expand the scope of the chemistry of nitro and thiol compounds, since the sulfonamides are expected to find extensive applications.

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