Collect. Czech. Chem. Commun.
2000, 65, 555-560
https://doi.org/10.1135/cccc20000555
Helical Phenanthrenes, Part 5. Synthesis of Pentahelicene-7,8-dione via Intramolecular Benzoin Condensation
Anja Modler-Spreitzer, Rainer Fritsch and Albrecht Mannschreck*
Institut für Organische Chemie, Universität Regensburg, D-93040 Regensburg, Germany
Abstract
The intramolecular benzoin condensation of [1,1'-binaphthyl]-2,2'-dicarbaldehyde (5), followed by oxidation with air, provides a new synthesis of (MP)-pentahelicene-7,8-dione (1). With reference to the original preparation of this quinone via acyloin condensation, its present yield (73% for the ring-closing step) is considerably increased.
Keywords: Benzoin condensation; Helicenediones; Pentahelicene-7,8-dione; Helicenes; Quinones; Binaphthyls; Helicity.
References: 16 live references.
