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Issue 29, 2017
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Regioselective Diels–Alder reaction to open-cage ketolactam derivatives of C60

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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.

Graphical abstract: Regioselective Diels–Alder reaction to open-cage ketolactam derivatives of C60

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Publication details

The article was received on 02 Jun 2017, accepted on 28 Jun 2017 and first published on 28 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01347G
Citation: Org. Biomol. Chem., 2017,15, 6136-6146
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    Regioselective Diels–Alder reaction to open-cage ketolactam derivatives of C60

    T. Tanaka, R. Nojiri, Y. Sugiyama, R. Sawai, T. Takahashi, N. Fukaya, J. Choi and Y. Kabe, Org. Biomol. Chem., 2017, 15, 6136
    DOI: 10.1039/C7OB01347G

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