ol9b01756_si_001.pdf (24.12 MB)

Site-Selectivity of Prato Additions to C70: Experimental and Theoretical Studies of a New Thermodynamic Product at the dd-[5,6]-Junction

Download (24.12 MB)
journal contribution
posted on 14.06.2019, 13:37 by Korinne Liosi, Adrian Romero-Rivera, Olesya Semivrazhskaya, Caravaggio D. Caniglia, Marc Garcia-Borràs, Nils Trapp, Sílvia Osuna, Yoko Yamakoshi
Three Prato monoadduct isomers were synthesized and structurally characterized by 1H, 13C NMR spectra and single-crystal X-ray diffraction, and one adduct on the dd-[5,6]-bond was found as the first example of a Prato [5,6]-adduct of C70. To investigate the mechanism in the generation of this dd-[5,6]-adduct, computational studies were employed to show that it was thermodynamically obtained by sigmatropic rearrangement from the presumed initial kinetic product de-[6,6]-adduct.