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Synfacts 2010(11): 1237-1237
DOI: 10.1055/s-0030-1258730
DOI: 10.1055/s-0030-1258730
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
Cascade Cycloadditions for the Synthesis of Perylenes
Contributor(s):Timothy M. Swager, Shuang LiuFurther Information
Publication History
Publication Date:
21 October 2010 (online)
Key words
Diels-Alder cycloaddition - domino reaction - polycyclic aromatic hydrocarbons - perylenes
Significance
Perylene derivatives were prepared by cascade [4+2] cycloadditions between 1,8-difurylnaphthalene and arynes. The double Diels-Alder reaction proceeds in a highly stereoselective fashion and only the exo,exo-diastereomer (3a-c) is formed as confirmed by X-ray crystallographic studies.
Comment
The synthetic method allows facile preparation of extended perylenes, which are potential molecular electronic materials. Further study on substituted derivatives with better solubility and stability is desirable.