4.6 Article

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

Journal

ELECTROCHIMICA ACTA
Volume 302, Issue -, Pages 310-315

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.electacta.2019.02.041

Keywords

Oxidative coupling; Anode; Rearrangement; Polycyclic arenes; Electrolysis

Funding

  1. German Research Foundation DFG, Center for INnovative and Emerging Materials [WA 1276/15-1]
  2. Carl-Zeiss-Stiftung
  3. Graduate School of Excellence MAterial Science IN MainZ (MAINZ)

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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. (C) 2019 Elsevier Ltd. All rights reserved.

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