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.
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-trimethanotriphenylene and Diels-Alder reactivity of the syn isomer / Borsato, G.; De, Lucchi; Fabris, O.; Lucchini, F.; Pasqualotti, V.; Zambon, Alfonso. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - (2003), pp. 561-563. [10.1016/S0040-4039(02)02533-9]
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-trimethanotriphenylene and Diels-Alder reactivity of the syn isomer
ZAMBON, Alfonso
2003
Abstract
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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