Zinc dust-mediated reductive degradation of decabromodiphenyl ether

Liu, Guobin; Zhao, Hongyun; Yang, Boguang; Thiemann, Thies

doi:10.1080/17518250903393882

Cited by 4 publications

(3 citation statements)

References 40 publications

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“…Prepared according to the general procedure above on a 0.51 mmol-scale and a 0.51 mmol-scale and obtained in 56% (0.071 g) and 57% (0.072 g) isolated yields, respectively, as a colorless oil (56% average of two runs). Spectroscopic data were consistent with those previously reported …”

Section: Methodssupporting

confidence: 91%

Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts

Sundalam

Stuart

2015

J. Org. Chem.

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The base mediated coupling of aliphatic alcohol pronucleophiles with unsymmetric diaryliodonium salt electrophiles is described. This metal-free reaction is operationally simple, proceeds at mild temperature, and displays broad substrate scope to generate industrially important alkyl-aryl ethers in moderate to excellent yield. The synthetic utility of these reactions is demonstrated, and aspects of sustainability are highlighted by the use of unsymmetric aryl(mesityl)iodonium arylating reagents.

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Section: Methodssupporting

confidence: 91%

Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts

Sundalam

Stuart

2015

J. Org. Chem.

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“…In the case of substrates substituted with bromine or iodine upon reduction of corresponding oximes, debromination and deiodination were observed (for a representative example see Figure S4). The reductive dehalogenation upon action of zinc powder in basic and acidic media was already described, and also includes the reaction carried out by zinc dust in the presence of ammonium formate and base (mainly NaOH) [50,51].…”

Section: Chemistrymentioning

confidence: 99%

Phosphonic Acid Analogs of Fluorophenylalanines as Inhibitors of Human and Porcine Aminopeptidases N: Validation of the Importance of the Substitution of the Aromatic Ring

et al. 2020

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A library of phosphonic acid analogs of phenylalanine substituted with fluorine, chlorine and trifluoromethyl moieties on the aromatic ring was synthesized and evaluated for inhibitory activity against human (hAPN) and porcine (pAPN) aminopeptidases. Fluorogenic screening indicated that these analogs are micromolar or submicromolar inhibitors, both enzymes being more active against hAPN. In order to better understand the mode of the action of the most active compounds, molecular modeling was used. It confirmed that aminophosphonic portion of the enzyme is bound nearly identically in the case of all the studied compounds, whereas the difference in activity results from the placement of aromatic side chain of an inhibitor. Interestingly, both enantiomers of the individual compounds are usually bound quite similarly.

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“…However, recent research also reported residues of BDE-209 in seafood . Major transformation routes of decaBDE were identified to be induced by UV light ,, or zerovalent metals , and after exposure to chemical reduction agents such as sodium borohydride . In addition, biotic transformation was reported to occur in sediment bacteria ,, and in fish. − …”

Section: Introductionmentioning

confidence: 99%

Hydrodebromination of Decabromodiphenyl Ether (BDE-209) in Cooking Experiments with Salmon Fillet

Bendig

Blumenstein

Hägele

et al. 2012

J. Agric. Food Chem.

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Polybrominated diphenyl ethers (PBDEs) are environmental contaminants regularly detected in biota and food. Seafood has been identified as the major dietary source for human uptake. Fish is predominantly consumed after cooking, and this process may alter the actual human intake of contaminants. This study thus aimed to investigate the fate of PBDEs in this cooking process. Heating of fish fortified with 2,2',3,3',4,4',5,5',6,6'-decabromodiphenyl ether (BDE-209) at typical cooking conditions (200 °C, in plant oil) resulted in a decrease of its concentration in favor of the formation of lower brominated congeners. After 15 min, ∼25% of BDE-209 was transformed into nona- to octabrominated congeners. The major transformation route was BDE-209 → BDE-206 → BDE-196 and BDE-199. Low amounts of heptabrominated congeners as well as one hexabromodibenzofuran and a heptabromodibenzofuran isomer were also detected. However, penta- and tetrabrominated diphenyl ethers were not observed, and heating of BDE-47 did not produce new transformation products.

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Zinc dust-mediated reductive degradation of decabromodiphenyl ether

Abstract: Zinc dust serves as a reducing agent in the presence of ammonium formate and NaOH, and is highly effective for the hydrodebromination of decabromodiphenyl ether to give diphenyl ether and the less brominated diphenyl ethers.

Cited by 4 publications

References 40 publications

Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts

Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts

Phosphonic Acid Analogs of Fluorophenylalanines as Inhibitors of Human and Porcine Aminopeptidases N: Validation of the Importance of the Substitution of the Aromatic Ring

Hydrodebromination of Decabromodiphenyl Ether (BDE-209) in Cooking Experiments with Salmon Fillet

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