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22
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33644500926
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note
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2O-phenyl-) could be bound to either of the two α-carbon atoms of each pyrrolidine ring, which gives four combinations, and (2) the tertiary carbons to which the tether is attached are chiral. Thus, there could be as many as 16 theoretically possible tether linkages between the two pyrrolidine rings, depending on the symmetry of the bisaddition pattern. Numerous attempts to obtain crystals of bisadducts isomers suitable for X-ray crystallographic analysis failed.
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Tan, X.1
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25
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0028765756
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Theoretical calculations have been used in the structure determination of fullerene bisadducts: (a) Hirsch, A.; Lamparth, I.; Grosser, T.; Karfunkel, H. R. J. Am. Chem. Soc. 1994, 116, 9385.
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28
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33644522913
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Reference 12b
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(f) Reference 12b.
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31
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33644534668
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note
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See Supporting Information for the AMI energy calculation of all bisadduct isomers with use of the Spartan 04 by Wavefunction. Given the endothermicity of the present reaction, this thermodynamic argument can be readily transformed into a kinetic one by virtue of the Hammond postulate.
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33
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(b) Wilson, S. R.; McMahon, S.; Tat, F. T.; Jarowski, P. D.; Schuster, D. I. Chem. Commun. 2003, 226.
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