p-Toluenesulfonyl azide → 2-Diazocyclohexanone
Reaction equation
C([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9])=O.C1(C)C=CC(S([N:19]=[N+:20]=[N-])(=O)=O)=CC=1>>[N+:19](=[C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9])=[N-:20]Participants
3
Procedure
Reaction of a formyl cyclohexanone derivative with para-toluenesulfonylazide effects displacement of the formyl group by a diazo moiety to provide a diazocyclohexanone derivative. For example, a formyl cyclohexanone derivative such as 2-phenyl-2-(2-cyanoethyl)-6-formylcyclohexanone can be reacted with about an equimolar quantity of para-toluene-sulfonylazide in the presence of dimethylamine or diethylamine, in an organic solvent such as diethyl ether, to provide, for instance, 2-phenyl-2-(2-cyanoethyl)-6-diazocyclohexanone.
Sources & evidence
- ORD record
- ord-7e1c2ed3e71246cab53e6551191ffa8b
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04141893
Reaction notes
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