Synthesis, structural characterization and photoisomerization of cyclic stilbenes

Abstract

Six cyclic stilbene derivatives with hindered free rotation around the C(vinyl)–C(phenyl) single bond were synthesized by McMurry coupling. The torsion angles around the double and the single bond, and the C=C bond length were obtained for many of the compounds from their solid-state structures. The photochemical isomerization was subsequently investigated for all derivatives under various conditions. The parent 1-(1-tetralinylidene)tetralin underwent efficient oxidative electrocyclization. The 2,2,2',2'-tetramethylated analogue was resistant towards photooxidation, however, its cis-isomer thermally reisomerized to the more stable trans-isomer.