Synthesis and crystal structure of 5,10-bis(phenylsulfonyl)tetrahydrodibenzopentalene
5,10-Bis(phenylsulfonyl)tetrahydrodibenzopentalene, C28H22O4S2, 1, was successfully synthesized via the photocatalyst-promoted hydrogenative transannulation of disulfonylcyclooctatetraene, 2, using perylene as the photocatalyst in the presence of (i-Pr)2NEt under UV-light irradiation (398 nm, 30 W)....
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2025-02-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | https://journals.iucr.org/paper?S205698902500060X |
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| author | Toshiki Sakami Hikaru Watanabe Takuma Sato Yasuhiro Okuda Kan Wakamatsu Haruo Akashi Akihiro Orita |
| author_facet | Toshiki Sakami Hikaru Watanabe Takuma Sato Yasuhiro Okuda Kan Wakamatsu Haruo Akashi Akihiro Orita |
| author_sort | Toshiki Sakami |
| collection | DOAJ |
| description | 5,10-Bis(phenylsulfonyl)tetrahydrodibenzopentalene, C28H22O4S2, 1, was successfully synthesized via the photocatalyst-promoted hydrogenative transannulation of disulfonylcyclooctatetraene, 2, using perylene as the photocatalyst in the presence of (i-Pr)2NEt under UV-light irradiation (398 nm, 30 W). In this reaction, the cyclooctatetraene moiety of 2 underwent hydrogenative transannulation, yielding 1. Single-crystal X-ray analysis revealed that both enantiomers of 1 are arranged alternately along the a axis of the unit cell. The structure features a wide V-shaped motif consisting of 6–5–5–6 fused rings, with a dihedral angle of approximately 97.2° between the planes of the terminal phenylene rings. Additionally, a pair of phenylsulfonyl groups were observed at the exo positions relative to the V-shaped array. |
| format | Article |
| id | doaj-art-4427eeed2cde480b97aad84ae763a835 |
| institution | Kabale University |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-4427eeed2cde480b97aad84ae763a8352025-02-06T07:27:16ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-02-0181217217610.1107/S205698902500060Xox2012Synthesis and crystal structure of 5,10-bis(phenylsulfonyl)tetrahydrodibenzopentaleneToshiki Sakami0Hikaru Watanabe1Takuma Sato2Yasuhiro Okuda3Kan Wakamatsu4Haruo Akashi5Akihiro Orita6Graduate School of Science and Engineering, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, JapanGraduate School of Science and Engineering, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, JapanGraduate School of Science and Engineering, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, JapanDepartment of Applied Chemistry, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, JapanDepartment of Chemistry, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, JapanResearch Institute of Frontier Science and Technology, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, JapanDepartment of Applied Chemistry, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan5,10-Bis(phenylsulfonyl)tetrahydrodibenzopentalene, C28H22O4S2, 1, was successfully synthesized via the photocatalyst-promoted hydrogenative transannulation of disulfonylcyclooctatetraene, 2, using perylene as the photocatalyst in the presence of (i-Pr)2NEt under UV-light irradiation (398 nm, 30 W). In this reaction, the cyclooctatetraene moiety of 2 underwent hydrogenative transannulation, yielding 1. Single-crystal X-ray analysis revealed that both enantiomers of 1 are arranged alternately along the a axis of the unit cell. The structure features a wide V-shaped motif consisting of 6–5–5–6 fused rings, with a dihedral angle of approximately 97.2° between the planes of the terminal phenylene rings. Additionally, a pair of phenylsulfonyl groups were observed at the exo positions relative to the V-shaped array.https://journals.iucr.org/paper?S205698902500060Xcrystal structuretransannulationethenyl sulfonehydrogenationtetrahydrodibenzopentalene |
| spellingShingle | Toshiki Sakami Hikaru Watanabe Takuma Sato Yasuhiro Okuda Kan Wakamatsu Haruo Akashi Akihiro Orita Synthesis and crystal structure of 5,10-bis(phenylsulfonyl)tetrahydrodibenzopentalene Acta Crystallographica Section E: Crystallographic Communications crystal structure transannulation ethenyl sulfone hydrogenation tetrahydrodibenzopentalene |
| title | Synthesis and crystal structure of 5,10-bis(phenylsulfonyl)tetrahydrodibenzopentalene |
| title_full | Synthesis and crystal structure of 5,10-bis(phenylsulfonyl)tetrahydrodibenzopentalene |
| title_fullStr | Synthesis and crystal structure of 5,10-bis(phenylsulfonyl)tetrahydrodibenzopentalene |
| title_full_unstemmed | Synthesis and crystal structure of 5,10-bis(phenylsulfonyl)tetrahydrodibenzopentalene |
| title_short | Synthesis and crystal structure of 5,10-bis(phenylsulfonyl)tetrahydrodibenzopentalene |
| title_sort | synthesis and crystal structure of 5 10 bis phenylsulfonyl tetrahydrodibenzopentalene |
| topic | crystal structure transannulation ethenyl sulfone hydrogenation tetrahydrodibenzopentalene |
| url | https://journals.iucr.org/paper?S205698902500060X |
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