Abstract Dehydrobenzoannulene derivatives 5− 7 containing isolated alkene linkages were synthesized by combining an in-situ Pd/Cu-mediated cross-coupling with an intramolecular cyclization strategy. 1 H NMR studies of these macrocycles and comparison with related systems verify that highly alkynylated dehydrobenzoannulenes possess weak induced ring currents, indicative of aromatic (4n+ 2 π-systems) and anti-aromatic (4n π-systems) ...
[Bell, Michael L; Chiechi, Ryan C; Johnson, Charles A; Kimball, David B; Matzger, Adam J; Brad Wan; Weakley, Timothy J.R; Haley, Michael M Tetrahedron, 2001 , vol. 57, # 17 p. 3507 - 3520]