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Synthesis 2000; 2000(13): 1839-1842
DOI: 10.1055/s-2000-8239
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Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes

S. M. Humayun Kabir* , Masahiko Iyoda
  • *Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan; Fax (880)8 21 71 52 57; E-mail: hkabir-che@sust.edu
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Publication Date:
31 December 2000 (online)

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The intramolecular coupling of benzoannelated zincacyclopentadiene using CuCl2 produced 1,8-dibromobiphenylene selectively in a good yield. On the contrary, the intermolecular coupling of zincacyclopentadiene produced 2,3,6,7,10,11,14,15-octamethoxytetraphenylene selectively in a synthetically reasonable yield under different reaction conditions. The reactions of 2,2′-dilithio-4,4′,5,5′-tetramethoxybiphenyl and 2,2′-dilithio-4,4′,5,5′-tetrakis(tert-butyldimethylsilyloxy)biphenyl with CuCl2 in THF unexpectedly produced the corresponding tetraphenylene derivatives, instead of the desired biphenylene derivatives. Octamethoxytetraphenylene was used to synthesize octaacetoxytetraphenylene in a quantitative yield either directly or through octahydroxytetraphenylene.

arenes - copper - zinc - intramolecular coupling - intermolecular coupling