Oxygen → 1-Nitroadamantane

HRID 992152

Reaktionsgleichung

Reaktionsgleichung von HRID 992152
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:11][N:12]1[C:16](=[O:17])[C:15]2=CC=CC=C2C1=O.[N+]([O-])=[O:24].FC(C1C=CC=CC=1)(F)F.[O:36]=O>C(#N)C>[N+:12]([C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)([O-:11])=[O:24].[C:1]12([OH:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:16]([O:17][C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)(=[O:36])[CH3:15]

Komponenten

9

Edukt 5

HCID 977OxygenHCID 7368(Trifluoromethyl)benzeneHCID 9238Adamantane2×HCID 10665N-HydroxyphthalimideHCID 178526396Nitrogen Dioxide

Produkt 3

HCID 641521-AdamantanolAusbeute 2 %HCID 641651-NitroadamantaneAusbeute 73 %HCID 5199731-Adamantyl acetateAusbeute 1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Into a flask, 1 mmole of adamantane, 0.05 mmole of N-hydroxyphthalimide, 15 mmole of nitrogen dioxide (NO2), 1 ml of acetonitrile and 2 ml of trifluoromethylbenzene were added and stirred for 5 hours at 60° C. in an atmosphere of oxygen. The reaction products were analyzed by gas chromatography, and, as a result, the conversion of adamantane was 90%, and nitroadamantane (yield 73%), adamantanol (yield 2%), acetyloxyadamantane (yield 1%) and adamantanone (yield 3%) were formed.

Quellen und Nachweise

ORD-Eintrag
ord-684f6da515db4ca99b2f29e56dd22d9f
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06468487B1

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