BIP! Finder - Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C2v-Symmetrical Pentakisadduct of C60

2018 • Cycloaddition Reactions of Azomethine Ylides and 1,3-Dienes on the C2v-Symmetrical Pentakisadduct of C60

Authors: Radoslav Z. Pavlović, Aleksandra Mitrović, William H. Coldren, Mira S. Bjelaković, Christopher M. Hadad, Veselin R. Maslak, Dragana R. Milić

Venue: The Journal of Organic Chemistry

Type: Publication

Abstract: 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-define... (read more)

Topics: Medicinal chemistry

DOI: 10.1021/acs.joc.7b03083

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External links: Crossref OpenAIRE

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