Reaction #74975

Reaction equation

3-Cyclohexene-1-carbonitrile

hexachlorocyclopentadiene

→

crude adduct

1,2,3,4,9,9-hexachloro-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene-6-carbonitrile

Conditions

Workup

1. 1
   Temperatureheated at 160°-170° C. for 6 hours
2. 2
   workup.DISTILLATIONvacuum distilled
3. 3
   Otherwas first removed

Procedure

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.

Source