title: Endohedral metal-induced regioselective formation of bis-Prato adduct of Y3N@I(h)-C80 and Gd3N@I(h)-C80.
abstract: Regioselective bisaddition of M3N@Ih-C80 (M = Y, Gd) was observed for the first time in the Prato reaction with N-ethylglycine and formaldehyde. The main kinetic bisadduct of Y3N@C80 was determined to be a [6,6],[6,6] adduct by (1)H and (13)C NMR and vis/NIR spectroscopy, and it converted to a mixture of regioisomers upon heating via a sigmatropic rearrangement. The main kinetic bisadduct of Gd3N@C80 (the [6,6],[6,6] adduct on the basis of vis/NIR data) existed stably under thermal conditions without isomerization. The likely position of the second addition of the Gd3N@C80 bisadduct was predicted by DFT calculations.
authors.affiliation: Laboratorium für Organische Chemie, ETH-Zürich , Vladimir-Prelog-Weg 3, CH-8093 Zürich, Switzerland.
authors.forename: Safwan
authors.initials: S
authors.lastname: Aroua
authors.forename: Marc
authors.initials: M
authors.lastname: Garcia-Borràs
authors.forename: Marc Florian
authors.initials: MF
authors.lastname: Bölter
authors.forename: Sílvia
authors.initials: S
authors.lastname: Osuna
authors.forename: Yoko
authors.initials: Y
authors.lastname: Yamakoshi
mesh_terms: D037741:Fullerenes / Q000737:chemistry*; D005682:Gadolinium / Q000737:chemistry*; D007700:Kinetics; D009584:Nitrogen / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D015019:Yttrium / Q000737:chemistry*
chemical_list: D037741:Fullerenes; D015019:Yttrium; D005682:Gadolinium; D009584:Nitrogen