A previously overlooked hydrodehalogenation reaction occurring during the multiple Pd0‐catalysed C−C coupling reaction between phenylacetylene and hexaiodo‐ and hexabromobenzene was found to give pentakis(phenylethynyl)benzene (“pentatolane”) as the major product, but no hexakis(phenylethynyl)benzene (“hexatolane”) under conditions previously claimed to yield the latter hydrocarbon. As an alternative to a viable route to hexatolane described in the literature, an independent synthesis of this hydrocarbon through sixfold Sonogashira coupling of hexakis(ethynyl)benzene with iodobenzene has been developed. Some physical and spectroscopic properties of hexatolane and of the hitherto unknown pentatolane have been determined after thorough purification by HPLC. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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A viable route to the novel globular cyclophane 2, a C 48 H 36 -spheriphane, is presented as a result of our research aimed at the synthesis of the hypothetical deciphenyl 3, a C 60 H 36 -spheriphane, which has been envisaged as a potential precursor to C 60 -fullerene. Several syntheses of the key intermediate of the route to 2, viz. septiphenyl 13 (C 48 H 42 ), a sterically crowded 1,3,5-tris(ortho-biphenylyl)benzene derivative, are described. These include threefold Heck coupling and related threefold Pd(0)-catalyzed C-C cross-coupling reactions, as well as threefold benzoannelation involving tetrachlorothiophene-S,S-dioxide and PET-induced dehalogenation of highly chlorinated septiphenyl derivatives.