Indirect electrooxidation of alcohols by a double mediatory system with two redox couples of [R2N+:O]/R2NO.cntdot. and [Br.cntdot. or Br+]/Br- in an organic-aqueous two-phase solution

Oxoammonium‐ and Nitroxide‐Catalyzed Oxidations of Alcohols

“…10,252,289 The so-called doxyl radical 45 decomposes on oxidation with m-CPBA, and the pyrroline and pyrrolidine radicals 46, 47, and 48 do not react with alcohols in the presence of a peracid 150 or in electrochemical reactions in the presence of bromide. 223 However, similar nitroxides have been converted to oxoammonium salts such as 7 and used for oxidations. 85,290 Nitroxides 49-54 were found to be unsatisfactory catalysts for bleach oxidations.…”

“…69). 222,223 A possible schematic of this reaction is presented in Scheme 8. In this scheme, note that the oxoammonium salts can also react with hydroxylamine to give nitroxide (Eq.…”

Electronic Records Research Working Meeting, May 28‐30, 1997: A Report from the Archives Community

“…The indirect electro‐oxidation in an undivided cell is based on a CH 2 Cl 2 /H 2 O two‐phase system employing two mediators. A systematic investigation of the different factors that affect the efficiency of the oxidation under these conditions has been carried out 51. The reaction conditions have been optimized by using a concentration of NaBr in the aqueous solution >15w %, a pH of 8.6 (saturated NaHCO 3 buffer solution), a concentration of the nitroxyl mediator in the organic phase ≥1 mol % with respect to the alcohol and a current density of 10–140 mA cm −2 with a Pt electrode.…”

Nitroxide‐Catalyzed Alcohol Oxidations in Organic Synthesis

“…35 On the other hand, neither the piperazine-based nitroxide 9, nor the morpholine-based systems 10 or 11 proved to be competent catalysts. 36,37 Likewise, the oxazole-and pyrrolidine-based systems 12-14, 38,39 and related systems, 40,41 failed to bring improvements over the oxidation catalysis by the parent TEMPO and closely related derivatives. Lastly, stereoselective reagents are sought.…”