Synthesis and crystal structure of 5,10-bis­(phenyl­sulfon­yl)tetra­hydro­dibenzo­penta­lene

Abstract

The structure of a curved 6–5–5–6 fused-ring system, with two benzene rings attached at both termini and a pair of phenyl­sulfonyl groups bonded to the two five-membered rings, is described.

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.