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Synthesis of the syn and anti isomer of 1,4,5,8,9,12-hexahydro-2,3,6,7,10,11-hexamethylidene-1,4:5,8:9,12-trimethano triphenylene and Diels–Alder reactivity of the syn isomer

✍ Scribed by Giuseppe Borsato; Ottorino De Lucchi; Fabrizio Fabris; Vittorio Lucchini; Marco Pasqualotti; Alfonso Zambon

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 111 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02533-9

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✦ Synopsis

The title compounds, new members in the class of tris-annelated benzenes with [2.2.1] bicyclic rings, were obtained in high yields by coupling of 2-bromo-3-trimethyltin-5,6-dimethylenenorborn-2-ene with copper(I) 2-thiophenecarboxylate (CuTC). The syn isomer was reacted with 3 equiv. of the dienophiles TCNE, DMAD, PTAD and norbornadiene to afford the corresponding cycloadducts.

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