title: Bis-1,3-dipolar Cycloadditions on Endohedral Fullerenes M3N@Ih-C80 (M = Sc, Lu): Remarkable Endohedral-Cluster Regiochemical Control.
abstract: In this work, we briefly report some attempts to control regioisomeric bisadditions on Sc3N@Ih-C80 and Lu3N@Ih-C80 using the tether-controlled multifunctionalization method. We then describe the use of independent (nontethered) bis-1,3-dipolar cycloaddition reactions and the characterization of 5 new bisadducts, 3 for Sc3N@C80 and 2 for Lu3N@C80, which have never been reported before. Unexpectedly and remarkably, 4 of these compounds exhibit relatively high symmetry and 2 of these bisadducts are the first examples of intrinsically chiral endohedral compounds, due to the addition pattern, not to the presence of chiral centers on the addends. Since an analysis of the statistically possible number of bisadduct isomers on an Ih-C80 cage has not been reported, we present it here.
authors: Department of Chemistry, University of Texas at El Paso , 500 West University Avenue, El Paso, Texas 79968, United States.
authors: Maira R
authors: MR
authors: Cerón
authors: Department of Chemistry, University of Texas at El Paso , 500 West University Avenue, El Paso, Texas 79968, United States.
authors: Marta
authors: M
authors: Izquierdo
authors: Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Universitat de Girona, Campus Montilivi, Facultat de Ciències , 17071 Girona, Spain.
authors: Marc
authors: M
authors: Garcia-Borràs
authors: Department of Chemistry, University of Texas at El Paso , 500 West University Avenue, El Paso, Texas 79968, United States.
authors: Sarah S
authors: SS
authors: Lee
authors: Department of Chemistry, Indiana-Purdue University at Fort Wayne , 2101 East Coliseum Boulevard, Fort Wayne, Indiana 46805, United States.
authors: Steven
authors: S
authors: Stevenson
authors: Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Universitat de Girona, Campus Montilivi, Facultat de Ciències , 17071 Girona, Spain.
authors: Sílvia
authors: S
authors: Osuna
authors: Department of Chemistry, University of Texas at El Paso , 500 West University Avenue, El Paso, Texas 79968, United States.
authors: Luis
authors: L
authors: Echegoyen