2019
DOI: 10.1021/acs.joc.9b00690
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Electrosynthesis ofN-Methylisatin

Abstract: Isatin in a solution of dry N,N-dimethylformamide/NaClO4 is electroreduced in the presence of CH3I. N-methylisatin (NMI) is obtained in quantitative molar yield and high current efficiency by controlled potential electrolysis (CPE). NMI and N-methylisatoic anhydride are the reaction products when CPE is performed in the absence of CH3I, but adding it once the CPE was completed. The water effect on the identity and yield of the reaction product(s) is investigated. Reaction pathways are proposed.

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Cited by 2 publications
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“…Mirı́fico et al investigated the electroreduction mechanism of isatin ( 35 , ISH) in 0.1 M NaClO 4 –DMF at a vitreous carbon electrode in the presence of CH 3 I (Scheme ). Through a one-electron process, 35 is reduced to 35 •– , which can react with either CH 3 I to afford NMI ( 37 ) or 35 to afford ISH – ( 35 – ) and ISH 2 • ( 36 ).…”
Section: Use Of Analytical Methods To Determine Reaction Pathways And...mentioning
confidence: 99%
“…Mirı́fico et al investigated the electroreduction mechanism of isatin ( 35 , ISH) in 0.1 M NaClO 4 –DMF at a vitreous carbon electrode in the presence of CH 3 I (Scheme ). Through a one-electron process, 35 is reduced to 35 •– , which can react with either CH 3 I to afford NMI ( 37 ) or 35 to afford ISH – ( 35 – ) and ISH 2 • ( 36 ).…”
Section: Use Of Analytical Methods To Determine Reaction Pathways And...mentioning
confidence: 99%