Malononitrile → 2-Ethenylcyclopropane-1,1-dicarbonitrile
Reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].O1[CH2:10][CH2:9][CH2:8][CH2:7]1>[Ag]=O>[C:3]([C:2]1([C:1]#[N:5])[CH2:10][CH:9]1[CH:8]=[CH2:7])#[N:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 3-liter glass vessel was charged with 250 g of 1,3-butadiene and 500 ml of n-hexane, and with vigorous stirring, 500 g of bromine was added dropwise at -15 to -25° C. over 6 hours to give 310 g of 1,4-dibromobutene-2. Furthermore, a 3-liter glass vessel was charged with 800 ml of tetrahydrofuran, 92 g of malononitrile, 325 g of silver oxide and 300 g of the 1,4-dibromobutene-2. These compounds were reacted by the method described in Journal of the American Chemical Society, 88 (9), 1979 (1966) to give 51 g of 1,1-dicyano-2-vinylcyclopropane.
Workup
- customThese compounds were reacted by the method
Sources & evidence
- ORD record
- ord-58b216f83c014195bf3fbd7133dae219
- Source dataset
- uspto-grants-1991_05
- Patent number
- US05019630
Reaction notes
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