Adamantane → 1-Nitroadamantane

HRID 992155Notes

Reaction equation

HRID 992155 reaction equation
[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]1C(=O)C2=CC=CC=C2C1=O.[O:23]=O.O=O>C(O)(=O)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:23]

Participants

5

Reactant 3

HCID 9238Adamantane2×HCID 10665N-HydroxyphthalimideHCID 131723558oxygen O2

Product 1

HCID 641651-NitroadamantaneYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a flask, 1 mmole of adamantane, 0.1 mmole of N-hydroxyphthalimide, 0.0005 mmole of acetylacetonatomanganese(II) Mn(AA)2 and 5 ml of acetic acid were added to mix and the flask was equipped with a gas bag (about 1L) of nitrogen monoxide NO. The mixture was reacted for 8 hours at 100° C. with stirring. The reaction products were analyzed by gas chromatography, and, as a result, the conversion of adamantane was 95%, and nitroadamantane (yield 75%) was formed.

Workup

  1. additionto mix
  2. customThe mixture was reacted for 8 hours at 100° C.

Sources & evidence

ORD record
ord-d1db4d9bdbb64884bc75d168098f52f1
Source dataset
uspto-grants-2002_10
Patent number
US06468487B1

Reaction notes

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