Concise Synthesis of Halogenated Chrysenes ([4]Phenacenes) that Favor π-Stack Packing in Single Crystals
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- Hiroyuki Isobe
- Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578, Japan, and Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
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- Shunpei Hitosugi
- Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578, Japan, and Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
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- Taisuke Matsuno
- Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578, Japan, and Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
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- Takeaki Iwamoto
- Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578, Japan, and Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
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- Junji Ichikawa
- Department of Chemistry, Tohoku University, Aoba-ku, Sendai 980-8578, Japan, and Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan
書誌事項
- 公開日
- 2009-08-10
- 資源種別
- journal article
- DOI
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- 10.1021/ol901693y
- 公開者
- American Chemical Society (ACS)
この論文をさがす
説明
A concise synthesis of halogenated chrysene derivatives from 2,2,2-trifluoroethyl tosylate and halostyrene was established. Friedel-Crafts type cyclization of a 1,1-difluoro-1-alkene bearing halogenated phenyl moieties involved skeletal rearrangement and dehydrogenation to afford the title compound in good to moderate yield. X-ray analysis revealed that the halogen substituents induce pi-stack packing of the molecules in the crystals.
収録刊行物
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- Organic Letters
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Organic Letters 11 (17), 4026-4028, 2009-08-10
American Chemical Society (ACS)
