HCCP is electrophilic. It degrades in base. Alcoholysis affords ketals C5Cl4(OR)2. HCCP readily undergoes Diels-Alder reactions with alkenes. This reaction is used to produce pesticides such as Aldrin (named after the reaction) and Isodrin. Most of these pesticides are no longer commercially available and banned by the Stockholm convention on persistent organic pollutants due to their toxicity to humans and animals. Biodegradation In surface water, photolysis is the most common reaction route, with a degradation half-life of 2 to 4 minutes. Deeper under water where less light penetrates hydrolysis and biodegradation are prominent pathways. The figure below gives an indication of possible degradation pathways when HCCPD is released into the environment. Light, water and oxygen can cause a double bond to oxidize to give a ketone structure, which can then undergo a ring-opening and form pentachlorodienoic acid, which forms two butadiene species with the release of carbon dioxide. However, this is only a minor pathway.
Hexachlorocyclopentadiene
Butylated hydroxytoluene
Triphenylchloroethylene
Beta-Hexachlorocyclohexane
Triphenylbromoethylene
Alpha-Hexachlorocyclohexane
Desmethylchlorotrianisene
Vinyl chloride