2 0 0 0 OA Electrochemical Synthesis of Dibenzothiophene S,S-Dioxides from Biaryl Sulfonyl Hydrazides
- 著者
- Yasuyuki OKUMURA Eisuke SATO Koichi MITSUDO Seiji SUGA
- 出版者
- The Electrochemical Society of Japan
- 雑誌
- Electrochemistry (ISSN:13443542)
- 巻号頁・発行日
- vol.91, no.11, pp.112007, 2023-11-28 (Released:2023-11-28)
- 参考文献数
- 34
The electrochemical synthesis of dibenzothiophene S,S-dioxides was achieved by the anodic oxidation of biaryl sulfonyl hydrazides. The use of Bu4NOTf as the electrolyte in HFIP/CH3NO2 (15 : 1) is essential. Several biaryl sulfonyl hydrazides followed by dibenzothiophene S,S-dioxides under mild electrochemical conditions. Control experiments and density functional theory calculations suggested that the electrooxidation of biaryl sulfonyl hydrazides would generate sulfonyl radicals or sulfonyl cations which were converted to dibenzothiophene S,S-dioxides.
2 0 0 0 OA Cathodic N–O Bond Cleavage of N-Alkoxy Amide
- 著者
- Eisuke SATO Sayaka OGITA Koichi MITSUDO Seiji SUGA
- 出版者
- The Electrochemical Society of Japan
- 雑誌
- Electrochemistry (ISSN:13443542)
- 巻号頁・発行日
- vol.91, no.11, pp.112005, 2023-11-28 (Released:2023-11-28)
- 参考文献数
- 26
Cathodic reduction efficiently cleaved N–O bonds. The simple cathodic reduction of Weinreb amides in a divided cell afforded the corresponding amide in good yields. Cyclic voltammetry experiments and density functional theory calculations suggested that the direct reduction of the N-methoxy amide generates the methoxy radical and amide anion. The release of methanol derived from methoxy radical would be the driving force of the N–O bond cleavage.