Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 12, Issue 27, Pages 7246-7253Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200600575
Keywords
[60]fullerene; amino acids; cycloaddition; reaction mechanisms; tertiary amines
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Thermal reactions of [60]fullerene with amino acid ester hydrochlorides and triethylamine in o-dichlorobenzene at reflux afforded pyrrolidinofullerene derivatives containing the CH,CH moiety and originating from triethylamine through an unusual C-N bond cleavage. Detailed investigation of these thermal reactions resulted in the discovery of unprecedented reactions between C-60 and tertiary amines and of reactions Of C-60 with tertiary amines and aldehydes, giving cyclopentafullerene derivatives with high stereoselectivity. Plausible reaction mechanisms for the product formation involving the uncommon C-N bond cleavage of tertiary amines were proposed on the basis of extensive experimental results.
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