Regioselective functionalization of sumanene

Doubly functionalized dioxosumanene was designed and synthesized to extend π conjugation bi-directionally. Friedel–Crafts double cycloalkylation to sumanene proceeded selectively to give the cycloalkylated compound. This compound was suggested to be the flattened structure as compared to sumanene, w...

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Bibliographic Details
Published in:Tetrahedron 2015-09, Vol.71 (35), p.5906-5909
Main Authors: Amaya, Toru, Ito, Takanori, Katoh, Shun, Hirao, Toshikazu
Format: Article
Language:English
Subjects:
Bowl-to-bowl inversion
Friedel–Crafts alkylation
Sumanene
π Bowl
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Summary:Doubly functionalized dioxosumanene was designed and synthesized to extend π conjugation bi-directionally. Friedel–Crafts double cycloalkylation to sumanene proceeded selectively to give the cycloalkylated compound. This compound was suggested to be the flattened structure as compared to sumanene, which induced the facile bowl-to-bowl inversion. Oxidation of the benzylic position was performed, and then a carbonyl group at the reverse side of the cycloalkylated arene was selectively protected with acetal to afford the doubly functionalized dioxosumanene. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.05.086