Electrochemical reduction of N-bromosuccinimide. Reaction mechanism for formation of the succinimidyl radical

Tuning Reactivity and Electronic Properties through Ligand Reorganization within a Cerium Heterobimetallic Framework

“…Using the measured E 1/2 value of 1 as a guide, E pa = -0.45 V vs Fc in THF, we expected that N-bromosuccinimide E pc = -0.37 V vs Fc in CH 3 CN, 16 and iodine, E pc = -0.140 V vs Fc in CH 3 CN, 17 could serve as mild oxidants. Treatment of 1 or 1-(DMEDA) with 1 equiv of N-halosuccinimide reagents (NXS; X = Cl, Br, I) or 0.5 equiv of iodine proceeded smoothly to Ce IV products.…”

2,4,4,6-Tetrabromocyclohexa-2,4-dienone: a new electron acceptor in the photosensitized oxidation of unsaturated substrates

“…The double action of TBCHD, as an electron acceptor and as a mild brominating agent, can be demonstrated, since the thermal reactions of (1) and/or (4) in acetonitrile solution with two equivalents of TBCHD slowly afford 1,2-dibromo-1,2-diphenylethyIene$ and rneso-dibromostilbene, respective-$ The oxidation waves at E, = 0.67 V and E, = 0.93 V result from the oxidation of the bromide anion (ref. 4). § The i.r.…”

Metal‐Free Electrochemical Oxidative Dihalogenation of Quinolines on the C5 and C7 Positions Using N‐Halosuccinimides

“…According to the experimental results and previous literature reported, [ 9c,9e,9f,9h,12,13 ] we proposed a feasible reaction mechanism as shown in Scheme 5. Firstly, the anode oxidation turned 1a into intermediate A through a deprotonation process, which was formed B via a spin delocalization.…”