Abstract
The problematic regioselective synthesis of fullerene bisadducts was finely solved by Diederich with the introduction of the tether-directed functionalization.[1] Since then, many other examples have been described, most of them using double Bingel addition or Diels-Alder cycloaddition reactions. Surprisingly, although 1,3-dipolar cycloaddition reactions are the most popular procedure for functionalization of C60, the use of this reaction for regioselective synthesis of fullerene bisadducts.Here we present our results of selective synthesis of trans-3 or e-bispirazolinofullerenes using bisnitrilimine tethered by di-tertbutylsilylbis(trifluoromethanesulfonate) group [3][4]. Further rupture of the silyl ester group allows the preparation of new derivatives for selected applications.[1] L.Isaacs, R.F.Haldimann,F.Diederich,Angew.Chem.Int.Ed.Engl.1994,33,2339. [2] F. Diederich, R. Kessinger. Acc. Chem. Res. 1999, 32, 537. [3] V. Cuesta, M. Urbani, P. de la Cruz, L. Welte, J.F. Nierengarten, F. Langa, Chem. Comm. 2016, 52, 13205 [4] R. Caballero, M. Barrejón, J. Cerdá, J. Aragó, S. Seetharaman, P. de la Cruz, E. Ortí, F. D’Souza, F. Langa. J. Am. Chem. Soc. 2021, 143, 11199. Figure 1
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