Regioselective Diels-Alder reaction to open-cage ketolactam derivatives of C60
Teruhiko Tanaka1, Ryuichi Nojiri1, Yoshiki Sugiyama1
1Department of Chemistry, Faculty of Science, Kanagawa University, 2946 Tsuchiya, Hiratsuka 259-1293, Japan. kabe@kanagawa-u.ac.jp.
Abstract:
Open-cage ketolactam fullerenes reacted with dienes on the rim of the orifice both regio- and stereoselectively. Unequivocal evidence for the structure of the Diels-Alder adduct was provided by 2D INADEQUATE 13C NMR studies on 13C enriched material, as well as via DFT-GIAO calculations. The theoretical calculations successfully model the regioselective and the endo stereoselective reaction, predicting molecular orbital control along with a repulsive steric interaction between the substituents on the nitrogen atom and those on the diene.
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