Reaction #74971

Reaction equation

1,2,3,4,9,9-hexachloro-1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione

n-butylmercaptan

→

6-butylthio-1,2,3,4,9,9-hexachloro-1,4,4a,6,7,8a-hexahydro-1,4-methanonaphthalene-5,8-dione

Solvents

benzene

Conditions

Workup

1. 1
   workup.DISSOLUTIONwere dissolved in 60 ml
2. 2
   OtherWhen the benzene was evaporated a white solid
3. 3
   Otherwas obtained
4. 4
   OtherOne recrystallization from benzene-Skelly B mixture
5. 5
   Otheryielded white crystals, m.p. 97°-98° C

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.

Source