Synthesis and Spectroscopic Studies of Expanded Planar Dehydrotribenzo [n] annulenes Containing One or Two Isolated Alkene Units

…, RC Chiechi, TJR Weakley, MM Haley

Index: Wan, W. Brad; Chiechi, Ryan C.; Weakley, Timothy J. R.; Haley, Michael M. European Journal of Organic Chemistry, 2001 , # 18 p. 3485 - 3490

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Citation Number: 11

Abstract

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) ...

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