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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Bibliographic Details
Published in:Electrochimica acta 2019-04, Vol.302, p.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: Article
Language:English
Subjects:
Anode
Anodizing
Aromatic compounds
Electrolysis
Isomerization
Oxidative coupling
Polycyclic arenes
Reagents
Rearrangement
Selectivity
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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