S. K. Sadhukhan, C. Viala, A. Gourdon
Jul 1, 2003
Citations
0
Influential Citations
6
Citations
Journal
Synthesis
Abstract
The syntheses of four hexabenzo[bc,ef,hi,kl,no,qr]coronene (HBC) derivatives have been carried out. Double Knoevenagel condensation of the benzil 5 with the ketone 6 gave the 2,3,4,5-tetrakis(4-tert-butylphenyl)cyclopenta-2,4-dien-1-one (7). Diels-Alder addition of 7 with di(4-tert-butylphenyl)acetylene, 4-[(4-tert-butylphenyl)ethynyl]-1,1′-biphenyl (9) or 1-tert-butyl-4-(phenylethynyl)benzene (11) gave the substituted hexaphenylbenzene 8, 10 and 12 which were cyclodehydrogenated to yield 1, 2 and 3, respectively. Similarly, condensation of 5 with dibenzylketone yielded the cyclopentadienone 13 which gave, by cycloaddition with di-(4-tert-butylphenyl)acetylene, the tetrasubstituted hexaphenylbenzene 14 which was cyclodehydrogenated to furnish 4.