Synthesis and crystal structure of 5,10-bis-(phenyl-sulfon-yl)tetra-hydro-dibenzo-penta-lene

Toshiki Sakami; Hikaru Watanabe; Takuma Sato; Yasuhiro Okuda; Kan Wakamatsu; Haruo Akashi; Akihiro Orita

doi:10.1107/S205698902500060X

Synthesis and crystal structure of 5,10-bis-(phenyl-sulfon-yl)tetra-hydro-dibenzo-penta-lene

Acta Crystallogr E Crystallogr Commun. 2025 Jan 28;81(Pt 2):172-176. doi: 10.1107/S205698902500060X. eCollection 2025 Feb 1.

Authors

Toshiki Sakami¹, Hikaru Watanabe¹, Takuma Sato¹, Yasuhiro Okuda², Kan Wakamatsu³, Haruo Akashi⁴, Akihiro Orita²

Affiliations

¹ Graduate School of Science and Engineering Okayama University of Science, 1-1 Ridai-cho Kita-ku Okayama 700-0005 Japan.
² Department of Applied Chemistry Okayama University of Science, 1-1 Ridai-cho Kita-ku Okayama 700-0005 Japan.
³ Department of Chemistry Okayama University of Science, 1-1 Ridai-cho Kita-ku Okayama 700-0005 Japan.
⁴ Research Institute of Frontier Science and Technology Okayama University of Science, 1-1 Ridai-cho Kita-ku Okayama 700-0005 Japan.

Abstract

5,10-Bis(phenyl-sulfon-yl)tetra-hydro-dibenzo-penta-lene, C₂₈H₂₂O₄S₂, 1, was suc-cessfully synthesized via the photocatalyst-promoted hy-dro-genative transannulation of di-sulfonyl-cyclo-octa-tetra-ene, 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 cyclo-octa-tetra-ene moiety of 2 underwent hy-dro-genative transannulation, yielding 1. Single-crystal X-ray analysis revealed that both enanti-omers 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 phenyl-ene rings. Additionally, a pair of phenyl-sulfonyl groups were observed at the exo positions relative to the V-shaped array.

Keywords: crystal structure; ethenyl sulfone; hydrogenation; tetrahydrodibenzopentalene; transannulation.