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Unexpected Diels-Alder reaction of [60]fullerene with electron-deficient ferrocenes as cyclopentadiene surrogates.
- Source :
-
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2021 Dec 09; Vol. 57 (98), pp. 13389-13392. Date of Electronic Publication: 2021 Dec 09. - Publication Year :
- 2021
-
Abstract
- The unexpected Diels-Alder reaction of [60]fullerene (C <subscript>60</subscript> ) with ferrocenes bearing electron-withdrawing groups as cyclopentadiene surrogates has been developed to selectively afford single isomers of [2 + 4] cycloadducts of C <subscript>60</subscript> . Mechanistic studies indicate that cyclopentadienes are in situ generated from electron-deficient ferrocenes in the presence of an oxidant and an acid, followed by [2 + 4] cycloadditions with dienophiles. A Michael addition reaction using a Grignard reagent has been utilized to transform the Diels-Alder adducts of C <subscript>60</subscript> into more stable fullerene derivatives.
Details
- Language :
- English
- ISSN :
- 1364-548X
- Volume :
- 57
- Issue :
- 98
- Database :
- MEDLINE
- Journal :
- Chemical communications (Cambridge, England)
- Publication Type :
- Academic Journal
- Accession number :
- 34825247
- Full Text :
- https://doi.org/10.1039/d1cc05749a