Products and reaction paths in the liquid phase oxidation of trans-1,2-dichloroethene with oxygen

Ultraviolet initiated liquid phase oxidation of neat trans-1,2-dichloroethene (1a) with oxygen at 30 °C afforded ca. 45% of the combined Cl-products CO, CO2, and phosgene as well as nine oxygenated and nine non-oxygenated chlorinated organic products. Major oxygenated products were cis- and trans-2,3-dichlorooxirane (6a, b) and 1,2,2-trichloroethyl formate (13); minor products were e.g., meso and rac bis(1,2,2-trichloroethyl) ether (11c, d) and dichloromethyl 1,2,2-trichloroethyl ether (12). The mode of formation of all products is rationalized by a unified reaction scheme.