Tetrahedron letters

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 …

…, O De Lucchi, F Fabris, V Lucchini, M Pasqualotti…

Index: Borsato, Giuseppe; De Lucchi, Ottorino; Fabris, Fabrizio; Lucchini, Vittorio; Pasqualotti, Marco; Zambon, Alfonso Tetrahedron Letters, 2003 , vol. 44, # 3 p. 561 - 563

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Citation Number: 18

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.