Electrochemical cleavage of 1,2-diphenylethanes at boron-doped diamond electrodes

Zollinger, Daniel; Griesbach, Ulrich; Pütter, Hermann; Comninellis, Christos

doi:10.1016/j.elecom.2004.04.014

Cited by 32 publications

(23 citation statements)

References 3 publications

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“…The selective C-C bond cleavage in bibenzyls and stilbenes [9] was established as a new reaction principle (scheme 1, Figure 1). Reaction products are the corresponding acetals.…”

Section: Oxidation In Nonaqueous Electrolytementioning

confidence: 99%

“…All experiments were performed under galvanostatic conditions using undivided cells except the oxidation of 1 and reduction of 9, which were carried out in a divided cell equipped with NafionÒ 117 or 324 (DuPont, USA) membranes using a Gossen Konstanter 34GU60R5,5 rectifier. We have previously described the experimental setup for oxidation of 3, 5 and 6 [8,9]. NMR investigations were carried out with a Bruker Avance 400 MHz.…”

Section: Generalmentioning

confidence: 99%

“…for pharmaceuticals. We have previously reported that the central C-C single or double bond in bibenzyls and stilbenes can be cleaved selectively using BDD anodes and MeOH/H 2 SO 4 /H 2 O as the electrolyte [9].…”

Section: Introductionmentioning

confidence: 99%

“…With regard to organic electrosyntheses on a preparative scale however, only few examples have been reported [5][6][7][8][9]. Selective transformations in aqueous electrolytes are difficult since complete degradation to carbon dioxide and/or unspecific formation of oxidation products like carboxylic acids are observed frequently [10].…”

Section: Introductionmentioning

confidence: 99%

“…methanol, the desired transformations like side chain oxidations [8], functional group conversions [6] and C-C bond cleavages [9] can be carried out selectively. Here we report the successful transfer of the concept of selective benzylic C-C bond cleavage on BDD anodes using a MeOH/ H 2 SO 4 /H 2 O electrolyte to polynuclear arenes like phenanthrene 5 an 9,10-dihydrophenanthrene 6 as substrates.…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of boron doped diamond electrodes for organic electrosynthesis on a preparative scale⋆

et al. 2005

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We have investigated some anodic and cathodic transformations using boron doped diamond (BDD) electrodes. The oxidation of a propargylic alcohol as well as the aromatic side chain oxidation in water as electrolyte did not yield the desired products in high yield and selectivity and led mainly to the formation of CO 2 due to electrochemical incineration of the starting material. With methanol as electrolyte, however, the reactivity of BDD electrodes is similar to graphite in most anodic methoxylation reactions, but the inactive behaviour of BDD electrodes leads to a different reaction pathway possibly involving methoxyl radicals with charge transfer from the electrolyte. It has been found that at BDD anodes benzylic single and double bonds can be split yielding aromatic acetals and esters. With phenanthrenes as starting material, o,o¢-disubstituted biaryls were obtained. So the use of BDD electrodes provides an efficient and environmentally friendly access to this interesting class of compounds. The high H 2 overpotential of BDD cathodes enables smooth and selective reduction of functional groups like oximes. Due to the high chemical and mechanical stability of the diamond layer of today's electrodes, electrode lifetime as well as reproducibility of the electrosyntheses has improved markedly. Aqueous basic conditions, however, must be avoided for BDD anodes. These conditions result in degradation of the diamond surface.

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“…The selective C-C bond cleavage in bibenzyls and stilbenes [9] was established as a new reaction principle (scheme 1, Figure 1). Reaction products are the corresponding acetals.…”

Section: Oxidation In Nonaqueous Electrolytementioning

confidence: 99%

Section: Generalmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%