Butanethiol → 6-Butylthio-1,2,3,4,9,9-hexachloro-1,4,4a,6,7,8a-hexahydro-1,4-methanonaphthalene-5,8-dione
Reaction equation
[Cl:1][C:2]12[C:14]([Cl:16])([Cl:15])[C:5]([Cl:17])([CH:6]3[CH:11]1[C:10](=[O:12])[CH:9]=[CH:8][C:7]3=[O:13])[C:4]([Cl:18])=[C:3]2[Cl:19].[CH2:20]([SH:24])[CH2:21][CH2:22][CH3:23]>C1C=CC=CC=1>[CH2:20]([S:24][CH:8]1[CH2:9][C:10](=[O:12])[CH:11]2[CH:6]([C:5]3([Cl:17])[C:14]([Cl:15])([Cl:16])[C:2]2([Cl:1])[C:3]([Cl:19])=[C:4]3[Cl:18])[C:7]1=[O:13])[CH2:21][CH2:22][CH3:23]Participants
4
Procedure
20 g. of 1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione, prepared as in Example 1, were dissolved in 60 ml. of benzene and then 10 g. of n-butylmercaptan and a few crystals of ferric chloride were added. This reaction mixture was shaken for 24 hours (Parr shaker). When the benzene was evaporated a white solid was obtained. One recrystallization from benzene-Skelly B mixture yielded white crystals, m.p. 97°-98° C. The infrared spectrum showed strong carbonyl at 1750 cm-1.