@article{SchnitzleinZhuShoyamaetal.2022, author = {Schnitzlein, Matthias and Zhu, Chongwei and Shoyama, Kazutaka and W{\"u}rthner, Frank}, title = {π-Extended Pleiadienes by [5+2] Annulation of 1-Boraphenalenes and ortho-Dihaloarenes}, series = {Chemistry - A European Journal}, volume = {28}, journal = {Chemistry - A European Journal}, number = {61}, doi = {10.1002/chem.202202053}, url = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-293919}, year = {2022}, abstract = {Palladium-catalyzed [5+2] annulation of 1-boraphenalenes with ortho-dihaloarenes afforded negatively curved π-extended pleiadienes. Two benzo[1,2-i:4,5-i']dipleiadienes (BDPs) featuring a seven-six-seven-membered ring arrangement were synthesized and investigated. Their crystal structure revealed a unique packing arrangement and theoretical calculations were employed to shed light onto the dynamic behavior of the BDP moiety and its aromaticity. Further, a naphthalene-fused pleiadiene was stitched together by oxidative cyclodehydrogenation to yield an additional five-membered ring. This formal azulene moiety led to distinct changes in optical and redox properties and increased perturbation of the aromatic system.}, language = {en} }