N-Nitrosodiethylamine → Bicyclo[2.2.1]hept-2-ene-1-carbonitrile
Reaction equation
N([N:3]([CH2:6][CH3:7])CC)=O.[CH2:8]1[CH:12]2C3C=C[CH:15]([CH:11]2[CH:10]=[CH:9]1)C3.C(#N)C=C>>[C:6]([C:7]12[CH2:15][CH:11]([CH2:12][CH2:8]1)[CH:10]=[CH:9]2)#[N:3]Participants
Procedure
Example 1 was repeated except that N-nitrosodiethylamine was used in place of N-nitrosodiphenylamine. N-nitrosodiethylamine was added to a mixed solution of dicyclopentadiene and acrylonitrile in an amount of 0.005% by weight. As a result, cyanonorbornene was continuously obtained with an average yield of 93% by mole. In this example, the amount of the soluble polymer produced was 0.01% by weight at the beginning of the reaction, which did not change significantly in 60 days after the initiation of the reaction. In addition , the operation was stopped after 80 days from the initiation to inspect in detail the inlet for the raw material, the inner wall, the outlet for the reaction solution and the-stirrer of the autoclave. No insoluble polymer was found to adhere to those surfaces.
Sources & evidence
- ORD record
- ord-24e5eb401eef406f849487cc7dd2c942
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05861528
Reaction notes
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