Dien‐katalysierte Photo‐Dimerisierung über Excimere (Exciplexe) oder Dienaddition an Anthracen und 9‐Phenylanthracen?

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Abstract
Diene‐Catalyzed Photodimerization via Excimers (Exciplexes) or Diene Addition to Anthracene and 9‐PhenylanthraceneThe [4 + 4]‐photodimerization of anthracene (1) is not enhanced by 2,4‐hexadiene (3) but impeded due to formation of [4 + 2]‐ (4) and [4 + 4]‐adducts (5, 6). 6 and 1 combine to give the bisadduct 7 at room temperature. The selective photolysis of 9‐phenylanthracene (8) leads to the anti‐[4 + 4]‐dimer (9). This can be compared with the [4 + 4]‐photodimerization of 9‐methylanthracene which affords the anti‐ and the thermolabile syn‐product. 1,3‐Dienes such as 1,3‐pentadiene (10) or 1,3‐cyclohexadiene (13) are not necessary for the formation of 9 but undergo cycloadditions with 8 to yield [4 + 2]‐ (11, 12, 14), [4 + 4]‐ (15), and [2 + 2]‐adducts (16, 17). The structures of the products are established primarily by high field 1H‐NMR spectroscopy.

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