The first buckybowl aryne. Corannulyne: a nonplanar benzyne.
[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.
Sygula
Andrzej
A
Department of Chemistry, Mississippi State University, Mississippi 39762, USA. asygula@chemistry.msstate.edu
Sygula
Renata
R
Rabideau
Peter W
PW