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Synfacts 2006(6): 0568-0568  
DOI: 10.1055/s-2006-934509
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Phenacenes from Diels-Alder Trapping of Photogenerated o-Xylylenols

Contributor(s): Timothy M. Swager, Mark S. Taylor
F. Ilhan, D. S. Tyson, M. A. Meador*
Ohio Aerospace Institute and NASA Glenn Research Center, Cleveland, USA
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Publikationsdatum:
19. Mai 2006 (online)

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Significance

The synthesis of bisimide derivatives of the phenanthrene and benzo[e]pyrene ring systems is described. Enol intermediates, generated by photoisomerization of ortho-substituted aryl ketones, participate efficiently in Diels-Alder cycloadditions with maleimide derivatives to furnish the polycyclic backbone. Dehydration and dehydrogenation steps complete the synthesis of the target compounds, which are obtained in good yields (see scheme).