The Addition Patterns of C60 Trisadducts Involving the Positional Relationships e and trans-n (n = 2–4): Isolation, Properties, and Determination of the Absolute Configuration of Tris(malonates) and Tris[bis(oxazolines)]

✍ Scribed by Francis Djojo; Andreas Hirsch; Stefan Grimme

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 953 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199911)1999:11<3027::aid-ejoc3027>3.0.co;2-s

✦ Synopsis

A series of regioisomeric trisadducts of C 60 (5-11, 14-18) analysis of their NMR spectra. The absolute configurations of the adducts with inherently chiral addition patterns could having the positional relationships e and trans-n (n = 2-4) resulting from successive additions of malonates or be determined either by comparison of the calculated and experimental CD spectra of the bis(oxazoline) adducts or bis(oxazolines) to [6,6]-double bonds of the fullerene framework has been isolated and characterized. The new with knowledge of the absolute configurations of the chiral bisadduct precursors containing bis(oxazoline) addends. The adducts 8-11 and 15-17 represent examples of unprecedented addition patterns. The addition patterns of CD spectra of the pairs of diastereomers with an enantiomeric addition pattern f A-15/ f C-15, f A-16/ f C-16, and the new trisadducts with C 2 , C s or C 1 symmetry have been assigned on the basis of the known positional relationships f A-18/ f C-18 show mirror image behavior and pronounced Cotton effects. of the addends in their precursor bisadducts, and those of the C 2 -or C s -symmetric representatives have been verified by

Examples of all such addition patterns have been re- [a] Institut für Organische Chemie der Universität Erlangen ample, 14 different trisadducts can be produced from a pre-Henkestraße 42, D