title: [2 + 2] cycloaddition reaction to Sc3N@I(h)-C80. The formation of very stable [5,6]- and [6,6]-adducts.
abstract: The [2 + 2] cycloaddition reaction of Sc(3)N@I(h)-C(80) with benzyne was successfully conducted for the first time. The reaction affords both the [5,6]- and [6,6]-monoadducts with a four-membered ring attached to the cage surface on 5,6- and 6,6-ring fusions, respectively. The compounds were characterized by MALDI-TOF, NMR, UV-vis-NIR spectroscopy and single-crystal X-ray structure determination. The electrochemical behavior of both monoadducts was investigated. The [5,6]-regioisomer displays reversible cathodic behavior similar to that observed for the fulleropyrrolidines with a 5,6-addition pattern. Surprisingly, the [6,6]-regioisomer also exhibits reversible cathodic behavior. The interconversion reaction of the isomers was also explored, and the results showed that both monoadducts are thermally very stable.
authors.affiliation: Department of Chemistry, University of Texas at El Paso, El Paso, Texas 79968, United States.
authors.forename: Fang-Fang
authors.initials: FF
authors.lastname: Li
authors.forename: Julio R
authors.initials: JR
authors.lastname: Pinzón
authors.forename: Brandon Q
authors.initials: BQ
authors.lastname: Mercado
authors.forename: Marilyn M
authors.initials: MM
authors.lastname: Olmstead
authors.forename: Alan L
authors.initials: AL
authors.lastname: Balch
authors.forename: Luis
authors.initials: L
authors.lastname: Echegoyen
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry; D018360:Crystallography, X-Ray; D004563:Electrochemistry; D037741:Fullerenes / Q000737:chemistry*; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D012538:Scandium / Q000737:chemistry*; D013057:Spectrum Analysis
chemical_list: D001555:Benzene Derivatives; D037741:Fullerenes; D009942:Organometallic Compounds; C524146:benzyne; D012538:Scandium