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Synthesis 2003(10): 1521-1525
DOI: 10.1055/s-2003-40526
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Syntheses of Hexabenzocoronene Derivatives

Subir K. Sadhukhan, Christine Viala, André Gourdon*
NanoScience Group, CEMES-CNRS, BP3447, 29 Rue J. Marvig, 31055 Toulouse, France
Fax: +33(562)257999; e-Mail: gourdon@cemes.fr;
Further Information

Publication History

Received 31 March 2003
Publication Date:
08 July 2003 (online)

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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.

Key words

arenes - ketones - cycloadditions - polycycles - dehydrogenations - Diels-Alder reactions

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1

Present address: Chembiotek Research Pvt. Ltd, Block-Bn, Plot-7, Sector-V, Salt Lake Electronic Complex, Calcutta 700 091, India

13

Gimzewski, J. K., unpublished results