Synthesis of 2‑Phospha[7]helicene, a Helicene with a Terminal Phosphinine Ring

A synthetic strategy toward phosphahelicenes containing a terminal phosphinine ring has been explored. The 4-phenyl-6-methyl-2-phospha[7]­helicene was prepared from starting 2-bromobenzo­[c]­phenanthrene in 12% overall yield in 12 steps. The synthetic approach involves introduction of the phosphorus...

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Published inOrganic letters Vol. 24; no. 26; pp. 4756 - 4761
Main Authors Beránek, Tomáš, Jakubec, Martin, Sýkora, Jan, Císařová, Ivana, Žádný, Jaroslav, Storch, Jan
Format Journal Article
LanguageEnglish
Published American Chemical Society 08.07.2022
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Summary:A synthetic strategy toward phosphahelicenes containing a terminal phosphinine ring has been explored. The 4-phenyl-6-methyl-2-phospha[7]­helicene was prepared from starting 2-bromobenzo­[c]­phenanthrene in 12% overall yield in 12 steps. The synthetic approach involves introduction of the phosphorus function prior to photocyclization forming the final helicene skeleton, followed by the formation of a phosphorus hexacycle. The structure of the first phosphahelicene with a terminal phosphinine ring was confirmed by X-ray crystallography.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01723