title: Tethered bisadducts of C60 and C70 with addends on a common hexagonal face and a 12-membered hole in the fullerene cage.
abstract: The regioselective synthesis of easily isolable pure bismethano derivatives of C60 and C70 with high steric congestion is described using 1,3-dibenzoylpropane bis-p-toluenesulfonyl hydrazone as the addend precursor. When the addition occurs at two [6,6] ring junctions within the same hexagon, bisadducts with mirror symmetry are obtained for both C60 and C70. When the addition occurs at two [5,6] ring junctions in C60, a symmetrical adduct is formed, which readily undergoes photo-oxygenation and ring opening to yield a fullerene with a hole in the cage. In this work, we also propose a simple and general system to name all of the possible [6,6] bisadduct isomers on C70.
authors.affiliation: †Department of Chemistry, University of Texas at El Paso, 500 West University Avenue, El Paso, Texas 79968, United States.
authors.forename: Maira R
authors.initials: MR
authors.lastname: Cerón
authors.affiliation: †Department of Chemistry, University of Texas at El Paso, 500 West University Avenue, El Paso, Texas 79968, United States.
authors.forename: Marta
authors.initials: M
authors.lastname: Izquierdo
authors.affiliation: ‡Department of Chemistry, University of California at Davis, One Shields Avenue, Davis, California 95616, United States.
authors.forename: Amineh
authors.initials: A
authors.lastname: Aghabali
authors.affiliation: †Department of Chemistry, University of Texas at El Paso, 500 West University Avenue, El Paso, Texas 79968, United States.
authors.forename: Juan A
authors.initials: JA
authors.lastname: Valdez
authors.affiliation: ‡Department of Chemistry, University of California at Davis, One Shields Avenue, Davis, California 95616, United States.
authors.forename: Kamran B
authors.initials: KB
authors.lastname: Ghiassi
authors.affiliation: ‡Department of Chemistry, University of California at Davis, One Shields Avenue, Davis, California 95616, United States.
authors.forename: Marilyn M
authors.initials: MM
authors.lastname: Olmstead
authors.affiliation: ‡Department of Chemistry, University of California at Davis, One Shields Avenue, Davis, California 95616, United States.
authors.forename: Alan L
authors.initials: AL
authors.lastname: Balch
authors.forename: Fred
authors.initials: F
authors.lastname: Wudl
authors.affiliation: †Department of Chemistry, University of Texas at El Paso, 500 West University Avenue, El Paso, Texas 79968, United States.
authors.forename: Luis
authors.initials: L
authors.lastname: Echegoyen
mesh_terms: D037741:Fullerenes / Q000737:chemistry*; D007536:Isomerism; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D037741:Fullerenes