TY - JOUR
T1 - Monofluorinated analogues of polybrominated diphenyl ethers as analytical standards: Synthesis, NMR, and GC-MS characterization and molecular orbital studies
AU - luthe, G.
AU - Leonards, P.E.G.
AU - Reijerink, G.S.
AU - Liu, H.L.
AU - Johansen, J.E.
AU - Robertson, L.W.
PY - 2006
Y1 - 2006
N2 - Polybrominated diphenyl ethers (PBDEs), a group of 209 individual congeners distinguishable by the number and position of bromines, are produced for use as flame retardants in consumer goods. PBDEs have become ubiquitous environmental contaminants, present in increasing levels in the environment and humans. In the present study, 10 individual monofluorinated analogues of PBDEs (F-PBDEs) and one difluorinated PBDE (FF-PBDE) were synthesized and characterized, and their gas chromatographic (GC) and mass spectrometric (MS) characteristics determined. The synthesis method utilized a nucleophilic reaction of bromophenols with diphenyliodonium salts and the perbromination of fluorosubstituted diphenyl ethers. Reaction yields were between 10% and 59% with ≥98% purity. Apart from the aromatic ring carrying the fluorine atom, only minor chemical nuclear magnetic resonance (NMR) shift changes were observed in comparison to the corresponding parent PBDEs, with the exception that the J
AB - Polybrominated diphenyl ethers (PBDEs), a group of 209 individual congeners distinguishable by the number and position of bromines, are produced for use as flame retardants in consumer goods. PBDEs have become ubiquitous environmental contaminants, present in increasing levels in the environment and humans. In the present study, 10 individual monofluorinated analogues of PBDEs (F-PBDEs) and one difluorinated PBDE (FF-PBDE) were synthesized and characterized, and their gas chromatographic (GC) and mass spectrometric (MS) characteristics determined. The synthesis method utilized a nucleophilic reaction of bromophenols with diphenyliodonium salts and the perbromination of fluorosubstituted diphenyl ethers. Reaction yields were between 10% and 59% with ≥98% purity. Apart from the aromatic ring carrying the fluorine atom, only minor chemical nuclear magnetic resonance (NMR) shift changes were observed in comparison to the corresponding parent PBDEs, with the exception that the J
UR - https://www.scopus.com/pages/publications/33646349475
UR - https://www.scopus.com/inward/citedby.url?scp=33646349475&partnerID=8YFLogxK
U2 - 10.1021/es052410z
DO - 10.1021/es052410z
M3 - Article
SN - 0013-936X
VL - 40
SP - 3023
EP - 3029
JO - Environmental Science and Technology
JF - Environmental Science and Technology
IS - 9
ER -
