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A Pirouette on a Metallofullerene Sphere:  Interconversion of Isomers of N-Tritylpyrrolidino Ih Sc3N@C80

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journal contribution
posted on 17.05.2006, 00:00 by Ting Cai, Carla Slebodnick, Liaosa Xu, Kim Harich, Thomas E. Glass, Christopher Chancellor, James C. Fettinger, Marilyn M. Olmstead, Alan L. Balch, Harry W. Gibson, Harry C. Dorn
The pure Ih 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.