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Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives

2009/03/16 by Jan Storch, Ján Sýkora, Jan Čermák +3 · 2 citations
Chemistry · Materials Science · #Photochromic and Fluorescence Chemistry #Porphyrin and Phthalocyanine Chemistry #Synthesis and Properties of Aromatic Compounds

paper · doi:10.1021/jo900077j

openalex publication_date 2009/03/16 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/22

Abstract

The new approach provides nonphotochemical syntheses of helicenes based on the easy, convergent, and modular assembly of key biphenylyl-naphthalenes and their platinum-catalyzed double cycloisomerization. This sequence of reactions provides a synthetic route to helicenes in two steps from simply accessible building blocks. Furthermore, the method enables the introduction of substituents into the hexahelicene skeleton. The strategy developed is exemplified by the synthesis of 6,10-dimethylhexahelicene and 1-methoxy-6,10-dimethylhexahelicene.

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