American Chemical Society
ol048548o_si_001.pdf (12.71 MB)

Tris(benzocyclobutadieno)triphenylene and Its Lower Biphenylene Homologues by Palladium-Catalyzed Cyclizations of 2,3-Didehydrobiphenylene

Download (12.71 MB)
journal contribution
posted on 2004-09-30, 00:00 authored by Beatriz Iglesias, Agustín Cobas, Dolores Pérez, Enrique Guitián, K. Peter C. Vollhardt
The Pd-catalyzed cycloaddition of didehydrobiphenylenes 2a,b, generated from the corresponding 3-(trimethylsilyl)-2-biphenylenyl triflates with fluoride, furnishes the C3-symmetric trimers 1a,b in which the embedded triphenylene unit is distorted to increase the aromaticity of the central benzene ring. Cocylization of 2a,b with dimethyl acetylenedicarboxylate provides the phenanthrene- and naphthalenecarboxylic ester analogues, depending on the catalyst used.