Regioselective Diels–Alder reaction to open-cage ketolactam derivatives of C60. Issue 29 (7th July 2017)

• Record Type: Journal Article
• Authors: Tanaka, Teruhiko; Nojiri, Ryuichi; Sugiyama, Yoshiki; Sawai, Ryouhei; Takahashi, Toshikazu; Fukaya, Norihisa; Choi, Jun-Chul; Kabe, Yoshio
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 29(2017)
• Page Start: 6136
• Page End: 6146
• Publication Date: 2017-07-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob01347g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Open-cage ketolactam fullerenes reacted with dienes on the rim of the orifice both regio- and endo-selectively, which were confirmed by 2D INADEQUATE 13 C NMR of 13 C enriched material/HMBC spectra as well as the theoretical calculations. 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 13 C NMR studies on 13 C 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.