The first buckybowl aryne. Corannulyne: a nonplanar benzyne.

Org Lett

Department of Chemistry, Mississippi State University, Mississippi 39762, USA.

Published: October 2005

[reaction: see text] Treatment of bromocorannulene with NaNH(2)/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). HDFT 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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http://dx.doi.org/10.1021/ol0519588DOI Listing

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