ChemInform Abstract: Photoinduced Molecular Rearrangements. The Photochemistry of 1,2,4-Oxadiazoles in the Presence of Sulfur Nucleophiles. Synthesis of 1,2,4-Thiadiazoles.
Abstract
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ChemInform Abstract
Irradiation of the oxadiazoles (I) in the presence of NaHS or thiols leads to the corresponding N-substituted benzamidines (II) by a photo-induced redox reaction at the ring O—N bond. In contrast, irradiation of (Ia) in the presence of thioureas or thiocarbamates affords the thiadiazoles (IV) and (VI), resp., by N—S bond formation with the S nucleophile. In the case of thioamides (VII), again the redox reaction predominates.
