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After a short irradiation period in acetonitrile at 302nm, the major photoproducts of BDE153 included 2,2′,4,4′,5-(BDE99), 2,2′,4,5,5′-(BDE101), and 2,4,4′,5,5′-(BDE118) substituted pentaBDEs as primary photohydrodebromination products, 2,2′,4,4′-(BDE47), 3,3′,4,4′-(BDE77), 2,3′,4,4′-(BDE66), and 2,2′,4,5′-(BDE49) substituted tetra-BDEs as secondary photohydrodebromination products, a suite of non-2,3,7,8-substituted mono- through penta-brominated dibenzofurans, and three tetrabrominated 2-hydroxybiphenyl congeners.
There is an incomplete understanding of their photochemistry because the majority of photoproducts, as indicated by incomplete mass balances, have not been identified.
1% yield) as minor photoproducts [eqn (1)].12,13 These ﬁndings also corrected earlier reports suggesting 3 was a secondary photoproduct of 5,14 thought at the time to be the primary photoproduct from 2.
Aqueous samples were then transferred to a separatory funnel, 100 mL of a saturated aqueous NaCl solution was added, and the solution was acidiﬁed to pH 2 to ensure any phenolic or acidic photoproducts were captured by extraction.
For reductive photodebromination of BDEs in hydrocarbon solvents such as methanol, THF, and toluene, there is first a photochemical homolytic aryl-bromine bond cleavage to yield an aryl radical and its bromine radical counterpart, which then either recombine within the solvent cage to yield no net reaction, or each subsequently abstract a hydrogen atom via ground state reactions from the organic solvent to give the photoreductively debrominated BDEs and HBr as primary photoproducts (3).
The utility of the model was then demonstrated on the known and assumed GC-RRTs of some of the chlorinated dihydroxybiphenyl and phenoxyphenol photoproducts of 2378-TeCDD, most of which do not have available analytical standards for conclusive structural identification.