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Synthesis of Single and Double Dibenzohelicenes via Rhodium‐Catalyzed Intramolecular [2+2+2] and [2+1+2+1] Cycloadditions

Dibenzo[7]helicenes were synthesized with up to 99% ee via the rhodium(I)/binap complex‐catalyzed enantioselective intramolecular [2+2+2] cycloaddition of 2‐phenylnaphthalene‐linked tryines. Additionally, [2+1+2+1] cycloaddition products, twisted anthracenes, were also synthesized by using difluorphos as a ligand. Although this compound is not configurationally stable at elevated temperature, the Scholl reaction of which afforded a configurationally stable double dibenzo[6]helicene. The thus obtained dibenzo[7]helicene exhibited good circularly polarized luminescence property and the double dibenzo[6]helicene exhibited high fluorescence quantum yield.

Authors:   Ryota Yamano, Yu Shibata, Ken Tanaka
Journal:   Chemistry - A European Journal
Year:   2018
Pages:   n/a
DOI:   10.1002/chem.201706008
Publication date:   19-Jan-2018
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  • anthracenes
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