US EPA

1744532 

Journal Article 

The addition of p-chlorobenzenethiol to isodrin 

Bird, CW; Khan, R 

1976 

1 

Tetrahedron Letters
ISSN: 0040-4039
EISSN: 1873-3581 

PESTAB/76/2933 

32 

2813-2814; 1976 

PESTAB. The room temperature addition of p-chlorobenzenethiol to isodrin in cyclohexane solution with free access of oxygen was studied. The sulfide fraction was oxidized to a mixture of the corresponding sulfoxides by iodobenzene dichloride in pyridine, and subsequent thin-layer chromatographic (tlc) separation gave two isomeric sulfoxides. These two sulfoxides, one of which contained the dichloroethylene grouping, were also present as such in the reaction mixture. The major reaction product was a ketone which on oxidation gave the corresponding sulfoxide. The identity of the hydroperoxide responsible for oxidation of the sulfides to sulfoxides is not known. Oxidation of isodrin also occurred during the reaction, yielding a half-cage ketone (presumably via rearrangement of endrin). The findings have implications for the environmental degradation of isodrin.