Synthesen und Strukturen von 2,5-Bis(2-arylvinyl)-1,4-benzochinonen und deren photochemisches Verhalten im Kristall / Syntheses and Crystal Structures of 2,5-Bis(2-arylvinyl)-1,4-benzoquinones and their Photochemical Reactivity in the Crystalline State

Abstract

The 2,5-bis(2-arylvinyl)-1,4-benzoquinones 1a-1e are formed from hydrolysis of their corresponding ketals 5 which are generated by anodic oxidation of the corresponding 1,4-dimethoxybenzene derivatives 4. The crystal structures of the quinone compounds 1a, 1d and 1e have been determined by X-ray analyses. The bond lengths of the quinone system are influenced by polar resonance structures. An α-type packing mode is observed for the three crystal structures of compounds 1. The vinylic double bonds have short intermolecular distances (1a: 4.417(5), 1d: 3.653(2), 1e: 4.224(5) Å). Only the crystals of 1d with the shortest contacts are photoreactive