Journal article
Endohedral metal-induced regioselective formation of bis-Prato adduct of Y3N@I(h)-C80 and Gd3N@I(h)-C80.
- Aroua S Laboratorium für Organische Chemie, ETH-Zürich , Vladimir-Prelog-Weg 3, CH-8093 Zürich, Switzerland.
- Garcia-Borràs M
- Bölter MF
- Osuna S
- Yamakoshi Y
- 2014-12-31
Published in:
- Journal of the American Chemical Society. - 2015
English
Regioselective bisaddition of M3N@Ih-C80 (M = Y, Gd) was observed for the first time in the Prato reaction with N-ethylglycine and formaldehyde. The main kinetic bisadduct of Y3N@C80 was determined to be a [6,6],[6,6] adduct by (1)H and (13)C NMR and vis/NIR spectroscopy, and it converted to a mixture of regioisomers upon heating via a sigmatropic rearrangement. The main kinetic bisadduct of Gd3N@C80 (the [6,6],[6,6] adduct on the basis of vis/NIR data) existed stably under thermal conditions without isomerization. The likely position of the second addition of the Gd3N@C80 bisadduct was predicted by DFT calculations.
- Language
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- English
- Open access status
- closed
- Identifiers
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- DOI 10.1021/ja511008z
- PMID 25549139
- Persistent URL
- https://roar.hep-bejune.ch/global/documents/88880
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