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60 by HPLC separation of diastereo- or enantiomers, see: a) Y. Nakamura, K. O-kawa, T. Nishimura, E. Yashima, J. Nishimura, J. Org. Chem. 2003, 68, 3251-3257;
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0033876762
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a) J. Jensen, J. Tejler, K. Wärnmark, J. Org. Chem. 2002, 67, 6008-6014;
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29
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0032834046
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60 can give various diastereoisomers with respect to the relative orientation of the ethoxycarbonyl residues at the two methanobridge atoms. There are three (in-in, in-out, and out-out) potential isomers for trans-2 and trans-4 adducts, trans-1 addition can yield two (out-out and in-out) diastereomers, and two out-out and two in-out diastereomers are possible for the e pattern. For a detailed discussion of in/out isomerism of bridged fullerene derivatives, see: a) J.-P. Bourgeois, P. Seiler, M. Fibbioli, E. Pretsch, F. Diederich, L. Echegoyen, Helv. Chim. Acta 1999, 82, 1572-1595;
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33
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0001400535
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f,sA (f = fullerene, s = systematic (numbering), C = clockwise, A = anticlockwise), see: a) C. Thilgen, A. Herrmann, F. Diederich, Helv. Chim. Acta 1997, 80, 183-199;
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36
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4544352325
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-
note
-
PM3 calculations were carried out with the Spartan program (SGI Version 5.1.3, Wavefunction Inc., 18 401 Von Karman Ave., Irvine, CA 92612 USA, 1998).
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