Investigations on isomerization and rearrangement of polycyclic arenes under oxidative conditions – Anodic versus reagent-mediated reactions

Electro-organic conversions at an active molybdenum anode enable the formation of fused arenes. High chemoselectivity was achieved under anodic conditions, and a reagent-induced selectivity was observed by comparison with results of MoCl5-mediated reactions. Polycyclic arenes like phenanthrenes, tri...

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Published inElectrochimica acta Vol. 302; pp. 310 - 315
Main Authors Beil, Sebastian B., Franzmann, Peter, Müller, Timo, Hielscher, Maximilian M., Prenzel, Tobias, Pollok, Dennis, Beiser, Nicole, Schollmeyer, Dieter, Waldvogel, Siegfried R.
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 10.04.2019
Elsevier BV
Subjects
Anode
Anodizing
Aromatic compounds
Electrolysis
Isomerization
Oxidative coupling
Polycyclic arenes
Reagents
Rearrangement
Selectivity
Polycyclic arenes
Anode
Electrolysis
Oxidative coupling
Rearrangement
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Summary:Electro-organic conversions at an active molybdenum anode enable the formation of fused arenes. High chemoselectivity was achieved under anodic conditions, and a reagent-induced selectivity was observed by comparison with results of MoCl5-mediated reactions. Polycyclic arenes like phenanthrenes, triphenylenes, chrysenes, or helicenes were selectively obtained in yields up to 87% and in some cases unusual rearrangements were crucial for the product formation. [Display omitted]
ISSN:0013-4686
1873-3859
DOI:10.1016/j.electacta.2019.02.041