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research article

First enantiomerically pure C70-adducts with a non-inherently chiral addition pattern

Kraszewska, Agnieszka
•
Rivera-Fuentes, Pablo
•
Thilgen, Carlo
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2009
New Journal of Chemistry

By addn. of an enantiomerically pure nitrile oxide to C70, four chiral isoxazolo[70]fullerene isomers were prepd. and isolated in pure state: two constitutional isomers resulting from addn. to one of the bonds radiating from the polar pentagons, and a constitutionally different pair of diastereoisomers resulting from addn. to a hexagon-hexagon fusion site parallel to the equator of the fullerene. After elimination of the stereogenic center from the side chain, the former two adducts become achiral, while the latter two are sep. transformed into enantiomeric fullerene derivs. with a non-inherently chiral addn. pattern as sole stereogenic element. In the present work, chiral [70]fullerene derivs. with a non-inherently chiral functionalization pattern were isolated in enantiomerically pure form for the first time. Their abs. configuration was assigned based on the good agreement between exptl. CD data and CD spectra calcd. using the ZINDO method.

  • Details
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Type
research article
DOI
10.1039/B814054E
Author(s)
Kraszewska, Agnieszka
Rivera-Fuentes, Pablo
Thilgen, Carlo
Diederich, Francois
Date Issued

2009

Published in
New Journal of Chemistry
Volume

33

Start page

386

End page

396

Subjects

(4 methoxybenzyl)oxyacetaldehyde

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[(4 methoxybenzyl)oxyl(phenyl)methyl)isoxazolo[4'

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5':7

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22](carbon70 d5h(6))[5

•

6]fullerene

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(methoxybenzyl)oxyacetaldehyde oxime

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3 [hydroxy(phenyl)methyl]isoxazolo[4'

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5':1

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9](carbon60 ih)[5

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6]fullerene

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3' [(4 methoxybenzyl)oxyl(phenyl)methyl)isoxazolo[4'

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5':8

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25](carbon70 d5h(6)[5

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6]fullerene

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3' (4 methoxybenzyl)oxylmethyl)isoxazolo[4'

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5':1

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9](carbon60 ih)[5

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6]fullerene

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3' [(4 methoxybenzyl0oxyl(phenyl)methyl)isoxazolo[4'

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5':25

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8](carbon70 d5h(6)[5

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6]fullerene

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3' benzoylisoxazolo[4'

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5':7

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22](carbon70 d5h(6))[5

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6]fullerene

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3' benzoylisoxazolol[4'

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5':1

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9](carbon60 ih)[5

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6]fullerene

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alcohol

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article

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carbon

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carbon nuclear magnetic resonance

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carbonyl derivative

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chirality

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circular dichroism

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cycloaddition

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diastereoisomer

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enantiomer

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isoxazolo[70]fullerene

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isoxazolofullerene asym prepn B3LYP CD ZINDO

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n hydroxy 2 [(4 methoxybenzyl)oxyl] 2 phenylethanimidoyl chloride

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nitric oxide

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nitrile oxide C70 addn

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priority journal

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proton nuclear magnetic resonance

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synthesis

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ultraviolet radiation

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unclassified drug

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LOCBP  
Available on Infoscience
October 30, 2019
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/162506
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