Djojo F, Hirsch A (1998)
Publication Type: Journal article, Original article
Publication year: 1998
Original Authors: Djojo F., Hirsch A.
Publisher: Wiley-VCH Verlag
Book Volume: 4
Pages Range: 344-356
Journal Issue: 2
DOI: 10.1002/(SICI)1521-3765(19980210)4:2<344::AID-CHEM344>3.0.CO;2-Y
In this paper we describe facile access to enantiomerically pure bis- and trisadducts of C with four different inherent chiral addition patterns, namely (f)C- and (f)A-I, II* (trans-2), (f)C- and (f)A-I, III* (trans-3), (f)C- and (f)AI, III*, III* (trans-3, trans-3, trans-3) and (f)C- and (f)A-I, eI, eII (e,e,e), obtained by cyclopropanation of [6,6] double bonds with C-symmetrical bisoxazolines and subsequent chromatographic separation of the corresponding diastereomers on achiral stationary phases. The CD spectra of the related pairs of diastereomers, whose addition patterns represent pairs of enantiomers, reveal pronounced Cotton effects and mirror-image behavior. It is the chiral arrangement of the conjugated π-electron system within the fullerene core itself that predominantly determines the chiroptical properties. We show that the magnitude of the Cotton effects strongly depends on the extent of chiral distortion of the π-electron system within the fullerene cage.
APA:
Djojo, F., & Hirsch, A. (1998). Synthesis and chiroptical properties of enantiomericaily pure bis- and trisadducts of C60 with an inherent chiral addition pattern. Chemistry - A European Journal, 4(2), 344-356. https://doi.org/10.1002/(SICI)1521-3765(19980210)4:2<344::AID-CHEM344>3.0.CO;2-Y
MLA:
Djojo, Francis, and Andreas Hirsch. "Synthesis and chiroptical properties of enantiomericaily pure bis- and trisadducts of C60 with an inherent chiral addition pattern." Chemistry - A European Journal 4.2 (1998): 344-356.
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