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Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C2v-Symmetrical Pentakisadduct of C60
Radoslav Z Pavlović1, Aleksandra Mitrović1, William H Coldren2
1Faculty of Chemistry, University of Belgrade , Studentski trg 16, P.O. Box 51, 11158 Belgrade, Serbia.
Abstract:
The reactivity of the C2v-symmetric pentakisadduct of C60 with azomethine ylides and conjugated dienes was studied experimentally and computationally. This derivative possesses four [6,6] double bonds, each with unique electrophilicity. The Diels-Alder reaction studied is a regiospecific, kinetically and thermodynamically guided [4 + 2] process producing [5:1]-hexaadducts with an octahedral addition pattern. The kinetically controlled Prato reaction gives a mixture of regioisomeric [5:1]-hexaadducts. The synthesis of geometrically well-defined supramolecular architectures may benefit from these new types of highly functionalized [5:1]-hexaadducts.
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