4.8 Article

The first buckybowl aryne. Corannulyne: A nonplanar benzyne

Journal

ORGANIC LETTERS
Volume 7, Issue 22, Pages 4999-5001

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol0519588

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[GRAPHICS] Treatment of bromocorannulene with NaNH2/tBuOK in THF in the presence of furans or amines leads to formation of addition products in good yields, presumably through formation of 1,2-didehydrocorannulene (corannulyne). HUT calculations predict that corannulyne exists as a bowl-shaped entity and that the didehydrogenation energy of corannulene is slightly lower than that of benzene.

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