Tether-directed selective synthesis of fulleropyrrolidine bisadducts.
Selective synthesis of C60 bisadducts has been achieved by using the Prato 1,3-dipolar cycloaddition of tethered bis-azomethine ylides. New bis(benzaldehydes) 1-4 tethered by a rigid linker were prepared and used to direct the second cycloaddition of azomethine ylide to C60. Equatorial, trans-4, trans-3, trans-2, and trans-1 bisadducts have been selectively prepared with this approach. However, the introduction of chiral centers in the pyrrolidine rings in the course of the reaction complicated the chemistry, as a number of stereoisomers theoretically could be formed. The structure determination of the isomeric bisadducts was made based on spectroscopic data and theoretical calculations. To our best knowledge, this represents the first example of a systematic study on tether-directed selective synthesis of C60 fulleropyrrolidine bisadducts.
Zhou
Zhiguo
Z
Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, USA. zhouz@lunainnovations.com
Schuster
David I
DI
Wilson
Stephen R
SR
D003432:Cross-Linking Reagents / Q000737:chemistry*; D037741:Fullerenes / Q000737:chemistry*; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D013057:Spectrum Analysis; D013237:Stereoisomerism
D003432:Cross-Linking Reagents; D037741:Fullerenes; D011760:Pyrrolidinones