Stereoisomer specific reaction of hexabromocyclododecane with reduced sulfur species in aqueous solutions

Concentrations and Long-Term Temporal Trends of Hexabromocyclododecanes (HBCDD) in Lake Trout and Walleye from the Great Lakes

“…54−57 Another reason for changes in isomer distributions between original chemical production and final environmental measurements is thermal rearrangement due to the high temperatures used when HBCDD is applied to materials. 14,56 The measured diastereomer distributions in lake trout and walleye from the Great Lakes are in agreement with prior measurements. The percent abundance (±standard deviation) of each isomer was 72% ± 13, 13% ± 7, and 15% ± 7 for α, β, and γ, respectively.…”

“…The HBCDD commercial mixture mainly contains three different diastereomers, α, β, and γ with approximate compositions of 10–13% of α-HBCDD, less than 12% of β-HBCDD, and 70–90% of γ-HBCDD. , Previous measurements suggest that this distribution changes to predominantly α-HBCDD in biota such as fish ,,, through the bioisomerization of β- and γ- to α-HBCDD that has a longer half-life . There are several pathways by which HBCDD can be metabolized including oxidation, reductive debromination, and dehydrogenation. − Another reason for changes in isomer distributions between original chemical production and final environmental measurements is thermal rearrangement due to the high temperatures used when HBCDD is applied to materials. , …”

A Caveat When Using Alkyl Halides as Tagging Agents to Detect/Quantify Reactive Sulfur Species

“…Analysis of reaction kinetics and initial products suggests that the reaction is SN2 nucleophilic substitution for MeI and 1,3-D but likely reductive dehalogenation for CP [ 24 ]. Zhang et al studied the reactions between H 2 S/HS n H and hexabromocyclododecane (HBCDD) [ 25 ]. They observed that both RSS chemicals can release bromine atoms from HBCDD via reductive debromination.…”