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Synthesis and Spectroscopic Studies of Expanded Planar Dehydrotribenzo[ n ]annulenes Containing One or Two Isolated Alkene Units
Author(s) -
Wan W. Brad,
Chiechi Ryan C.,
Weakley Timothy J. R.,
Haley Michael M.
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200109)2001:18<3485::aid-ejoc3485>3.0.co;2-i
Subject(s) - annulene , alkene , chemistry , intramolecular force , ring (chemistry) , aromaticity , stereochemistry , medicinal chemistry , computational chemistry , combinatorial chemistry , organic chemistry , molecule , catalysis
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 (4 n +2 π‐systems) and anti‐aromatic (4 n π‐systems) behavior, in spite of their large size and extensive benzannulation.