Oxygen → Bicyclo(2.2.1)heptan-2-one

Reaction equation

[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[CH:2]2.[O:8]=O>>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C:2]2=[O:8].[C:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

Reactant 2

HCID 977Oxygen

HCID 103522-Norbornene

Product 2

HCID 10345Bicyclo(2.2.1)heptan-2-oneYield 70%

HCID 51845401-Cyclohexene-1-carboxaldehydeYield 30%

Procedure

7.1 g norbornene and 1 atm O2 were passed over 100 mg of this material at 280° C. for 2 hours, yielding in a partial conversion 99 mg norbornanone (relative yield 70%) and 43 mg cyclohexene carboxaldehyde (relative yield 30%) with a turnover frequency of 160 moles total product per mole Rh per hr.

Sources & evidence

ORD record: ord-4bb6ecef8ce947c0a9f2a7776e14e54b
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05162285

Reaction notes

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