The pure I(h) isomer of Sc3N@C80 was allowed to react with N-triphenylmethyl-5-oxazolidinone via ... more The pure I(h) isomer of Sc3N@C80 was allowed to react with N-triphenylmethyl-5-oxazolidinone via the corresponding azomethine ylide. The reaction results in the formation of two monoadducts; one (1b) is the kinetic product, and the other (1a) is thermodynamically more stable. Small amounts of the bisadducts were also formed. The structure of the thermodynamic monoadduct 1a was shown conclusively by NMR spectroscopy and X-ray crystallography to result from addition across the 5,6-ring junction. The kinetic product 1b was demonstrated to be the 6,6-ring juncture adduct on the basis of NMR experiments and X-ray crystallography. In refluxing chlorobenzene pure 1b was converted to the more thermodynamically stable 1a isomer. These N-tritylpyrrolidino derivatives are potentially useful precursor compounds for further derivatization for various applications.
The first N-tritylpyrrolidino derivatives of D(3h) (78:5) Sc(3)N@C(78) were successfully synthesi... more The first N-tritylpyrrolidino derivatives of D(3h) (78:5) Sc(3)N@C(78) were successfully synthesized and isolated. The addition sites for the two nearly equivalent kinetic monoadducts 1a and 1b are across two different 6,6 junction sites on the Sc(3)N@C(78) cage that are offset from the horizontal plane defined by the Sc(3)N cluster. The adducts were characterized by NMR experiments, DFT calculations and X-ray crystallographic analysis of Sc(3)N@C(78) derivative 1a. A unique finding of this study is the regiocontrol of adduct docking by the internal Sc(3)N cluster.
The pure I(h) isomer of Sc3N@C80 was allowed to react with N-triphenylmethyl-5-oxazolidinone via ... more The pure I(h) isomer of Sc3N@C80 was allowed to react with N-triphenylmethyl-5-oxazolidinone via the corresponding azomethine ylide. The reaction results in the formation of two monoadducts; one (1b) is the kinetic product, and the other (1a) is thermodynamically more stable. Small amounts of the bisadducts were also formed. The structure of the thermodynamic monoadduct 1a was shown conclusively by NMR spectroscopy and X-ray crystallography to result from addition across the 5,6-ring junction. The kinetic product 1b was demonstrated to be the 6,6-ring juncture adduct on the basis of NMR experiments and X-ray crystallography. In refluxing chlorobenzene pure 1b was converted to the more thermodynamically stable 1a isomer. These N-tritylpyrrolidino derivatives are potentially useful precursor compounds for further derivatization for various applications.
The first N-tritylpyrrolidino derivatives of D(3h) (78:5) Sc(3)N@C(78) were successfully synthesi... more The first N-tritylpyrrolidino derivatives of D(3h) (78:5) Sc(3)N@C(78) were successfully synthesized and isolated. The addition sites for the two nearly equivalent kinetic monoadducts 1a and 1b are across two different 6,6 junction sites on the Sc(3)N@C(78) cage that are offset from the horizontal plane defined by the Sc(3)N cluster. The adducts were characterized by NMR experiments, DFT calculations and X-ray crystallographic analysis of Sc(3)N@C(78) derivative 1a. A unique finding of this study is the regiocontrol of adduct docking by the internal Sc(3)N cluster.
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