Hypochlorite reactions with aromatic hydrocarbons

Polycyclic aromatic hydrocarbons (PAH), which are ubiquitous in the environment, including surface waters, undergo facile chlorination by hypochlorite when dissolved in humus-poor water to give a suite of chlorinated PAH (1660). It is therefore conceivable that this chlorination can occur under natural conditions, but this is yet to be determined. Another new possible source of natural chlorinated PAH is the reported in vitro reaction of benzo [a pyrene diol epoxide, the ultimate carcinogen of benzo aIpyrene with chloride ion to give chlorohydrin DDD, which has been isolated and identified as an intermediate en route to a benzol a pyrene-DN A adduct (1661). However, DDD is not considered to be a natural compound at this time. 

---