Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C-2v-Symmetrical Pentakisadduct of C-60
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AuthorsPavlovic, Radoslav Z.
Coldren, William H.
Hadad, Christopher M.
Maslak, Veselin R.
Article (Published version)
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The reactivity of the C-2v-symmetric pentakisadduct of C-60 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.
Source:Journal of Organic Chemistry, 2018, 83, 4, 2166-2172
- Amer Chemical Soc, Washington