TY  - JOUR
A1  - Schnitzlein, Matthias
A1  - Zhu, Chongwei
A1  - Shoyama, Kazutaka
A1  - Würthner, Frank
T1  - π‐Extended Pleiadienes by [5+2] Annulation of 1‐Boraphenalenes and ortho‐Dihaloarenes
T2  - Chemistry – A European Journal
N2  - 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.
KW  - annulation
KW  - aromaticity
KW  - azulene
KW  - cyclodehydrogenation
KW  - polycyclic aromatic hydrocarbons
Y1  - 2022
UR  - https://opus.bibliothek.uni-wuerzburg.de/frontdoor/index/index/docId/29391
UR  - https://nbn-resolving.org/urn:nbn:de:bvb:20-opus-293919
VL  - 28
IS  - 61
ER  -