Hexachlorocyclopentadiene → 1,2,3,4,9,9-Hexachloro-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene-6-carbonitrile
Reaktionsgleichung
[CH:1]1([C:7]#[N:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.[Cl:9][C:10]1([Cl:19])[C:14]([Cl:15])=[C:13]([Cl:16])[C:12]([Cl:17])=[C:11]1[Cl:18]>>[Cl:15][C:14]12[C:10]([Cl:9])([Cl:19])[C:11]([Cl:18])([CH:3]3[CH:4]1[CH2:5][CH2:6][CH:1]([C:7]#[N:8])[CH2:2]3)[C:12]([Cl:17])=[C:13]2[Cl:16]Komponenten
3
Versuchsvorschrift
3-Cyclohexene-1-carbonitrile (Aldrich Chemical Corp.) (56 g.), and 200 g. of hexachlorocyclopentadiene were mixed, heated at 160°-170° C. for 6 hours, and then allowed to cool to room temperature. The reaction mixture was then vacuum distilled. Unreacted hexachlorocyclopentadiene was first removed and then the crude adduct produced was collected, 175°-170° C. at 0.3 m.m. Hg. The thick liquid was crystallized very slowly in Skelly "B". The crude solid melted at 140°-150° C.
Aufarbeitung
- temperatureheated at 160°-170° C. for 6 hours
- distillation