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-ter t-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 .
Key words
arenes - ketones - cycloadditions - polycycles - dehydrogenations - Diels-Alder reactions
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