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Reductive Benzylation of Singly Bonded 1,2,4,15-C60 Dimers with an Oxazoline or Imidazoline Heterocycle: Unexpected Formation of 1,2,3,16-C60 Adducts and Insights into the Reactivity of Singly Bonded C60 Dimers.
- Source :
-
Journal of Organic Chemistry . 4/3/2015, Vol. 80 Issue 7, p3566-3571. 6p. - Publication Year :
- 2015
-
Abstract
- Upon reduction, singly bonded 1,2,4,15-C60 dimers with an oxazoline or imidazoline heterocycle dissociate into monoanionic 1,2,4-C60 intermediates, which surprisingly leads to the formation of 1,2,3,16-C60 rather than 1,2,4,15-C60 adducts of the original configuration by further benzylation, even though the analogue of dibenzylated C60 oxazoline with a 1,2,4,15-configuration is stable and has been obtained. These results are corroborated by computational calculations, which rationalize the reaction and clarify the structure of the 1,2,3,16-C60 adducts, providing new insights into the intrinsic reactivity of singly bonded C60 dimers. [ABSTRACT FROM AUTHOR]
- Subjects :
- *DIMERS
*OXAZOLINE
*IMIDAZOLINES
*HETEROCYCLIC compounds
*ORGANIC chemistry research
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 80
- Issue :
- 7
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 102613077
- Full Text :
- https://doi.org/10.1021/acs.joc.5b00253