Anaerobic degradation of deca-brominated diphenyl ether contaminated in products: Effect of temperature on degradation characteristics.

In this study, a 200-day deca-brominated diphenyl ether (deca-BDE) degradation activity experiment was carried out, using consumer-use curtain material as the substrate. During the degradation process, polybrominated diphenyl ether (PBDE) products with fewer bromine atoms were gradually generated by the debromination of deca-BDE. The influences of temperature, initial substrate dosing mass, and pH were also investigated. Interestingly, thermophilic conditions proved more beneficial for deca-BDE degradation than mesophilic conditions. The results also demonstrate that the debromination rate increased with the initial deca-BDE dosing mass, and that pH 7 was the most suitable for the reaction.

Organochlorine and organobromine compounds in a benthic fish (Solea solea) from Bizerte Lagoon (northern Tunisia): implications for human exposure.

Information on the occurrence of persistent organic pollutants (POPs) in fish from Tunisia is scarce. In this study, thirty one persistent organic pollutants including organochlorine pesticides (OCPs) (dichlorodihenyltrichloroethane and its metabolites (DDTs), hexachlorocyclohexanes (HCHs) and hexachlorobenzene (HCB)), polychlorinated biphenyls (PCBs), polybrominated diphenyl ethers (PBDEs) and methoxylated polybrominated diphenyl ethers (MeO-PBDEs) were determined in solea solea muscle, from Bizerte Lagoon (northern Tunisia) and from the Mediterranean Sea (reference area) (northern Mediterranean). In the Bizerte Lagoon, contaminant concentrations generally followed this order: PCBs>DDTs>PBDEs>MeO-PBDEs>HCB>HCHs; while in the Mediterranean Sea, pollutant concentration followed this order: MeO-PBDEs>PCBs>DDTs>PBDEs>HCB>HCHs. Mean levels of organochlorine compounds were 1018 and 380 ng g(-1) lipid weight (lw) in fish from Bizerte Lagoon and the Mediterranean Sea, respectively. Mean concentrations of organobromine compounds were 279 and 301 ng g(-1) lw in sole from Bizerte Lagoon and the Mediterranean Sea, respectively. Organohalogen concentrations in fish from Bizerte Lagoon were similar or slightly lower than those reported for other marine fish species from other locations around the world. PCB, HCH, HCB and PBDE levels were negatively correlated with lipid content, while no such correlation was seen for DDTs. Assessment based on several available guidelines suggested an insignificant human health risk for dietary intake of HCB, lindane and PBDEs associated with consumption of sole. However, the estimated lifetime cancer risk from dietary exposure to DDTs and PCBs is a potential concern.

Carry-over of dietary organochlorine pesticides, PCDD/Fs, PCBs, and brominated flame retardants to Atlantic salmon (Salmo salar L.) fillets.

Information on carry-over of contaminants from feed to animal food products is essential for appropriate human risk assessment of feed contaminants. The carry-over of potentially hazardous persistent organic pollutants (POPs) from feed to fillet was assessed in consumption sized Atlantic salmon (Salmo salar). Relative carry-over (defined as the fraction of a certain dietary POP retained in the fillet) was assessed in a controlled feeding trial, which provided fillet retention of dietary organochlorine pesticides (OCPs), dioxins (PCDD/Fs), polychlorinated biphenyls (PCBs), and brominated flame retardants (BFRs). Highest retention was found for OCPs, BFRs and PCBs (31-58%), and the lowest retentions were observed for PCDD/Fs congeners (10-34%). National monitoring data on commercial fish feed and farmed Atlantic salmon on the Norwegian market were used to provide commercially relevant feed-to-fillet transfer factors (calculated as fillet POP level divided by feed POP level), which ranged from 0.4 to 0.5, which is a factor 5-10 times higher than reported for terrestrial meat products. For the OCP with one of the highest relative carry-over, toxaphene, uptake and elimination kinetics were established. Model simulations that are based on the uptake and elimination kinetics gave predicted levels that were in agreement with the measured values. Application of the model to the current EU upper limit for toxaphene in feed (50 µg kg(-1)) gave maximum fillet levels of 22 µg kg(-1), which exceeds the estimated permissible level (21 µg kg(-1)) for toxaphene in fish food samples in Norway.

Biodegradation of bromoamine acid using combined airlift loop reactor and biological activated carbon.

The biodegradation of bromoamine acid (BAA) in a combined airlift loop reactor (ALR) and biological activated carbon (BAC) system was investigated. The results showed that the ALR using Sphingomonas xenophaga as inoculum and granular activated carbon (GAC) as carrier, could run steadily for over 3 months at less than 950 mg L(-1) BAA. And the efficiencies of BAA decolorization and COD removal in ALR reached about 90% and 50% within 12h, respectively. When it was further aerated for another 12h, the ALR effluent gradually became yellow due to the auto-oxidation of BAA decolorization products which were identified by HPLC-MS. Further biotreatment of the ALR effluent using BAC showed that the efficiency of TOC removal could reach 90%. Moreover, the release efficiencies of Br(-) and SO(4)(2-) were 73.5% and 67.4%, respectively. It indicated that BAC system was effective in the biodegradation of the auto-oxidative BAA decolorization products.

Novel brominated flame retardants: a review of their analysis, environmental fate and behaviour.

This review summarises current knowledge about production volumes, physico-chemical properties, analysis, environmental occurrence, fate and behaviour and human exposure to the "novel" brominated flame retardants (NBFRs). We define the term NBFRs as relating to BFRs which are new to the market or newly/recently observed in the environment. Restrictions and bans on the use of some polybrominated diphenyl ether (PBDE) formulations, in many jurisdictions, have created a market for the use of NBFRs. To date, most data on NBFRs have arisen as additional information generated by research designed principally to study more "traditional" BFRs, such as PBDEs. This has led to a wide variety of analytical approaches for sample extraction, extract purification and instrumental analysis of NBFRs. An overview of environmental occurrence in abiotic matrices, aquatic biota, terrestrial biota and birds is presented. Evidence concerning the metabolism and absorption of different NBFRs is reviewed. Human exposure to NBFRs via different exposure pathways is discussed, and research gaps related to analysis, environmental sources, fate, and behaviour and human exposure are identified.

Regional contamination versus regional dietary differences: understanding geographic variation in brominated and chlorinated contaminant levels in polar bears.

The relative contribution of regional contamination versus dietary differences to geographic variation in polar bear (Ursus maritimus) contaminant levels is unknown. Dietary variation between Alaska, Canada, East Greenland, and Svalbard subpopulations was assessed by muscle nitrogen and carbon stable isotope (δ(15)N, δ(13)C) and adipose fatty acid (FA) signatures relative to their main prey (ringed seals). Western and southern Hudson Bay signatures were characterized by depleted δ(15)N and δ(13)C, lower proportions of C(20) and C(22) monounsaturated FAs and higher proportions of C(18) and longer chain polyunsaturated FAs. East Greenland and Svalbard signatures were reversed relative to Hudson Bay. Alaskan and Canadian Arctic signatures were intermediate. Between-subpopulation dietary differences predominated over interannual, seasonal, sex, or age variation. Among various brominated and chlorinated contaminants, diet signatures significantly explained variation in adipose levels of polybrominated diphenyl ether (PBDE) flame retardants (14-15%) and legacy PCBs (18-21%). However, dietary influence was contaminant class-specific, since only low or nonsignificant proportions of variation in organochlorine pesticide (e.g., chlordane) levels were explained by diet. Hudson Bay diet signatures were associated with lower PCB and PBDE levels, whereas East Greenland and Svalbard signatures were associated with higher levels. Understanding diet/food web factors is important to accurately interpret contaminant trends, particularly in a changing Arctic.

Bioaccumulation of several brominated flame retardants and dechlorane plus in waterbirds from an e-waste recycling region in South China: associated with trophic level and diet sources.

The present study is primarily designed to examine the role played by dietary sources on polybrominated diphenyl ethers (PBDE) congener profiles in waterbirds collected in an e-waste recycling region in South China. Some emerging halogenated flame retardants (HFRs), such as dechlorane plus (DP), 2,3,4,5,6-pentabromoethyl benzene (PBEB), pentabromotoluene (PBT), and 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE), were also quantified. Stable isotopes (δ(15)N and δ(13)C) were analyzed to assess the trophic levels and dietary sources of the birds. PBDEs were found to be the predominant HFRs, followed by DP, PBT, PBEB, and BTBPE. The birds in which BDE209 was predominant have differential δ(13)C and δ(15)N signatures compared with other birds, suggesting that dietary source is one of the important factors in determining the PBDE congener profile in birds. The levels of ΣPBDEs, PBEB, and PBT were significantly correlated with the trophic level (δ(15)N) for avian species which are located in a food chain, indicating the biomagnification potential of these compounds. No correlation was found between DP concentrations and trophic level of the birds. There is a significantly negative correlation between the fraction of anti-DP and δ(15)N, suggesting that the metabolic capability of DP in birds increases with the trophic level of the birds.

Modeling relationships between Baltic Sea herring (Clupea harengus) biology and contaminant concentrations using multivariate data analysis.

Baltic Sea herring (Clupea harengus) is a pelagic, zoo-planktivorous fish and young (2-5 years old) individuals of this species are sampled annually in the Swedish marine monitoring program. This study determined concentrations of organochlorines (OCs) and brominated flame retardants (BFRs) in dorsal muscle from herring (n = 60) of varying age (2-13 years), weight (25-200 g), and body length (16-29 cm) caught at three locations in the Swedish part of the Baltic Proper. In order to ensure that the fish biology was as varied as possible, though still similar from all sampling sites, the fish to be chemically analyzed were selected from a large number of fish with determined biology using Multivariate Design. In statistical evaluation of the data, univariate and multivariate data analysis techniques, e.g. principal components analysis (PCA), partial least-squares regression (PLS), and orthogonal PLS (OPLS), were used. The results showed that the fish are exposed to a cocktail of contaminants and levels are presented. Significant OPLS models were found for all biological variables versus concentrations of OCs and BFRs, showing that fish biology covaries with fish contaminant concentrations. Correlation coefficients were as high as 0.98 for e.g. ßHCH concentration (wet weight) versus the lipid content. Lastly, the OC concentrations in herring muscle were modeled against the BFR concentrations to determine whether concentrations of either could be used to predict the other. It was found that OPLS models allowed BFR concentrations to be predicted from OC concentrations with high, but varying, accuracy (R(2)Ys between 0.93 to 0.75). Thus, fish biology and contaminant concentrations are interwoven, and fish biological parameters can be used to calculate (predict) contaminant concentrations. It is also possible to predict the BFR concentrations in an individual fish from its concentrations of OCs with very high accuracy.

Brominated flame retardants and organochlorine contaminants in winter flounder, harp and hooded seals, and North Atlantic right whales from the Northwest Atlantic Ocean.

Various brominated flame retardants (BFRs), including polybrominated diphenyl ethers (PBDEs) and current-use, non-PBDE BFRs, as well as organochlorine (OC) pesticides and polychlorinated biphenyls (PCBs), were measured in winter flounder, harp and hooded seals, and North Atlantic right whales from the Eastern United States and Canada. The concentrations of PBDEs in winter flounder and right whales were similar in magnitude to the levels of PCBs, which was unlike the pattern observed in seals. In these marine mammals, the levels of PBDEs were orders of magnitude lower than the levels of OCs and PCBs detected. Evidence existed for the accumulation of methoxylated (MeO)-PBDEs of natural origin in seals and right whales. Current-use, non-PBDE BFRs (including hexabromocyclododecane, pentabromoethylbenzene, hexabromobenzene, and pentabromotoluene) were detected in winter flounder and marine mammals. Future research should focus on monitoring PBDEs, current-use, non-PBDE BFRs, and MeO-BDEs of natural origin in marine organisms from Massachusetts and Cape Cod Bays.

Improved detection of reactive metabolites with a bromine-containing glutathione analog using mass defect and isotope pattern matching.

Drug bioactivation leading to the formation of reactive species capable of covalent binding to proteins represents an important cause of drug-induced toxicity. Reactive metabolite detection using in vitro microsomal incubations is a crucial step in assessing potential toxicity of pharmaceutical compounds. The most common method for screening the formation of these unstable, electrophilic species is by trapping them with glutathione (GSH) followed by liquid chromatography/mass spectrometry (LC/MS) analysis. The present work describes the use of a brominated analog of glutathione, N-(2-bromocarbobenzyloxy)-GSH (GSH-Br), for the in vitro screening of reactive metabolites by LC/MS. This novel trapping agent was tested with four drug compounds known to form reactive metabolites, acetaminophen, fipexide, trimethoprim and clozapine. In vitro rat microsomal incubations were performed with GSH and GSH-Br for each drug with subsequent analysis by liquid chromatography/high-resolution mass spectrometry on an electrospray time-of-flight (ESI-TOF) instrument. A generic LC/MS method was used for data acquisition, followed by drug-specific processing of accurate mass data based on mass defect filtering and isotope pattern matching. GSH and GSH-Br incubations were compared to control samples using differential analysis (Mass Profiler) software to identify adducts formed via the formation of reactive metabolites. In all four cases, GSH-Br yielded improved results, with a decreased false positive rate, increased sensitivity and new adducts being identified in contrast to GSH alone. The combination of using this novel trapping agent with powerful processing routines for filtering accurate mass data and differential analysis represents a very reliable method for the identification of reactive metabolites formed in microsomal incubations.

Biotransformation of bromosesquiterpenes by marine fungi.

Biotransformation of bromosesquiterpenes was investigated with two types of fungi, Rhinocladiella atrovirens NRBC 32362 and also Rhinocladiella sp. K-001, isolated from the Okinawan brown alga Stypopodium zonale. R. atrovirens NRBC 32362 converted aplysistatin 1 into three compounds 5alpha-hydroxyaplysistatin 4, 5alpha-hydroxyisoaplysistatin 5 and 9beta-hydroxyaplysistatin 6. Transformation of 1, palisadin A 2 and 12-hydroxypalisadin B 3 by Rhinocladiella sp. K-001 gave two compounds, 3,4-dihydroaplysistatin 7 and 9,10-dehydrobromopalisadin A 8.

Trophodynamics of some PFCs and BFRs in a western Canadian Arctic marine food web.

The trophodynamics of per- and polyfluorinated compounds and bromine-based flame retardants were examined in components of a marine food web from the western Canadian Arctic. The animals studied and their relative trophic status in the food web, established using stable isotopes of nitrogen (delta15N), were beluga (Delphinapterus leucas) > ringed seal (Phoca hispida) > Arctic cod (Boreogadus saida) > Pacific herring (Clupea pallasi) approximately equal to Arctic cisco (Coregonus autumnalis) > pelagic amphipod (Themisto libellula) > Arctic copepod (Calanus hyperboreus). For the brominated diphenyl ethers, the lipid adjusted concentrations of the seven congeners analyzed (Sigma7BDEs: -47, -85, -99, -100, -153, -154, and -209) ranged from 205.4 +/- 52.7 ng/g in Arctic cod to 2.6 +/- 0.4 ng/g in ringed seals. Mean Sigma7BDEs concentrations in Arctic copepods, 16.4 ng/g (n = 2, composite sample), were greater than those in the top trophic level (TL) marine mammals and suggests that (i) Arctic copepods are an important dietary component that delivers BDEs to the food web and (ii) because these compounds are bioaccumulative, metabolism and depletion of BDE congeners in top TL mammals is an important biological process. There were differences in the concentration profiles of the isomers of hexabromocyclododecane (HBCD) in the food web. The most notable difference was observed for beluga, where the alpha-isomer was enriched (accounting for approximately 90% of the SigmaHBCD body burden), relative to its primary prey species, Arctic cod, where the alpha-isomer accounted for only 20% of the SigmaHBCD body burden (beta: 4% and gamma: 78%). For the C8-C11 perfluorinated carboxylic acids, the trophic magnification factors (TMFs) were all greater than unity and increased with increasing carbon chain length. PFOS and its neutral precursor, PFOSA, also had TMF values greater than one. There were also pronounced differences in the PFOSA to PFOS ratio in ringed seal (0.04) and in beluga (1.4) and suggests that, in part, there are differences in the efficacy of biotransforming PFOSA by whale and seal top predators that both preferentially feed on Arctic cod.

Some insights into how barnacles survive as sessile organisms.

During routine chemical analyses of the stalked ibliform barnacle Chaetolepas calcitergum Buckeridge & Newman 2006, peaks of more than 7% (by dry mass) of bromine were detected. Although bromine ions occur in seawater (up to 66 ppm), this level of accumulation, in the soft tissue of the barnacle, is extraordinary. Organic concentration of bromine compounds occurs in a number of invertebrates, such as algae and sponges, but this is the first record of elevated bromine in goose barnacles. The high accumulation of bromine compound(s) is most likely a defense mechanism. The present paper includes a review of the mechanisms deployed by barnacles to repel predators.

Long chain fatty acid uptake in vivo: comparison of [125I]-BMIPP and [3H]-bromopalmitate.

Insulin resistance is characterized by increased metabolic uptake of fatty acids. Accordingly, techniques to examine in vivo shifts in fatty acid metabolism are of value in both clinical and experimental settings. Partially metabolizable long chain fatty acid (LCFA) tracers have been recently developed and employed for this purpose: [9,10-3H]-(R)-2-bromopalmitate ([3H]-BROMO) and [125I]-15-(rho-iodophenyl)-3-R,S-methylpentadecanoic acid ([125I]-BMIPP). These analogues are taken up like native fatty acids, but once inside the cell do not directly enter beta-oxidation. Rather, they become trapped in the slower processes of omega and alpha-oxidation. Study aims were to (1) simultaneously assess and compare [3H]-BROMO and [125I]-BMIPP and (2) determine if tracer breakdown is affected by elevated metabolic demands. Catheters were implanted in a carotid artery and jugular vein of Sprague-Dawley rats. Following 5 days recovery, fasted animals (5 h) underwent a rest (n = 8) or exercise (n = 8) (0.6 mi/h) protocol. An instantaneous bolus containing both [3H]-BROMO and [125I]-BMIPP was administered to determine LCFA uptake. No significant difference between [125I]-BMIPP and [3H]-BROMO uptake was found in cardiac or skeletal muscle during rest or exercise. In liver, rates of uptake were more than doubled with [3H]-BROMO compared to [125I]-BMIPP. Analysis of tracer conversion by TLC demonstrated no difference at rest. Exercise resulted in greater metabolism and excretion of tracers with approximately 37% and approximately 53% of [125I]-BMIPP and [3H]-BROMO present in conversion products at 40 min. In conclusion, [3H]-BROMO and [125I]-BMIPP are indistinguishable for the determination of tissue kinetics at rest in skeletal and cardiac muscle. Exercise preferentially exacerbates the breakdown of [3H]-BROMO, making [125I]-BMIPP the analogue of choice for prolonged (>30 min) experimental protocols with elevated metabolic demands.

Natural production of organic bromine compounds in Berlin Lakes.

Berlin surface waters are characterized by elevated concentrations of organic bound bromine (up to 35 microg/L) in late summer. Organic bromine compounds in lakes are of significant importance because human life is closely connected to fresh water. Apart from recreational use, fresh water is frequently used for the production of drinking water, e.g., after bank filtration. Therefore the source, particularly the mechanism responsible for the formation is studied. Field studies indicate that the organic bromine compounds, measured as adsorbable organic bromine (AOBr), are autochthonous. Staggered maxima concentrations of chlorophyll-a, DOC and AOBr indicate that phototrophic organisms might contribute to the AOBr after death. The involvement of phototrophic organisms was established in the laboratory using surface water and/or cultures of organisms. Light and the presence of phototrophic organisms are essential for an AOBr production. Phototrophic organisms incorporate bromide, which is released randomly and after cell death. A part of the incorporated bromide is used for the formation of organic bromine compounds in the cell. After death of the organisms the brominated compounds and the incorporated bromide are released into the water phase, and an extracellular AOBr production can lead to a further formation of AOBr, most probably due to the parallel release of haloperoxidases.

Polybrominated hexahydroxanthene derivatives (PBHDs) and other halogenated natural products from the Mediterranean sponge Scalarispongia scalaris in marine biota.

Structures of polybrominated hexahydroxanthene derivatives (PBHDs) previously detected in commercial fish from the Mediterranean Sea and mussels from New Zealand were assigned to 2,7-dibromo-4a-bromomethyl-1,1-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene (TriBHD) and 2,5,7-tribromo-4a-bromomethyl-1,1-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthene (TetraBHD) by comparing their gas chromatography/mass spectrometry (GC/MS) features with isolates from an Australian sponge of the Cacospongia genus. Because of the geographic distance between the Mediterranean Sea in Europe (origin of the fish) and Australia (origin of the sponge), a closely related sponge, Scalarispongia scalaris, was collected in the Mediterranean Sea and analyzed for PBHDs and other halogenated compounds. The Mediterranean sponge contained the PBHDs at 37 mg/kg dry weight. Using quantitative standards for the first time, the PBHD concentrations in fish and mussel samples published earlier were re-examined. Concentrations of up to 1 mg/kg TriBHD and 0.5 mg/kg TetraBHD were determined in the lipids. No correlation with 2,2', 4,4', 5,5'-hexachlorobiphenyl (PCB 153) or p,p'-DDE was found, which is in agreement with other marine halogenated natural products detected in the fish samples. Besides the PBHDs, further unknown halogenated compounds were detected in the Mediterranean sponge, some of which were also detected in commercial fish. GC/electron ionization-MS analysis showed that a major mixed-halogenated compound in the sponge had a molecular ion at m/z 480 and contained three bromines, three chlorines, and 9-10 carbons. No corresponding structure has been described for this feature in the scientific literature. This sponge secondary metabolite and potential novel halogenated natural product was also detected in commercial fish. Another prominent mixed halogenated compound detected both in sponge and fish was the dibromotrichloro monoterpene MHC-1 (C(10)H(13)Br(2)Cl(3)).

Analysis of Ah receptor pathway activation by brominated flame retardants.

Brominated flame-retardants (BFRs) are used as additives in plastics to decrease the rate of combustion of these materials, leading to greater consumer safety. As the use of plastics has increased, the production and use of flame-retardants has also grown. Many BFRs are persistent and have been detected in environmental samples, raising concerns about the biological/toxicological risk associated with their use. Most BFRs appear to be non-toxic, however there is still some concern that these compounds, or possible contaminants in BFRs mixtures could interact with cellular receptors. In this study we have examined the interaction of decabromodiphenyl ether, Firemaster BP4A (tetrabromobisphenol A), Firemaster PHT4 (tetrabromophthalic anhydride), hexabromobenzene, pentabromotoluene, decabromobiphenyl, Firemaster BP-6 (2,2',4,4',5,5'-hexabromobiphenyl) and possible contaminants of BFR mixtures with the Ah receptor. Receptor binding and activation was examined using the Gel Retardation Assay and increased expression of dioxin responsive genes was detected using the reporter gene based CALUX assay. The results demonstrate the ability of BFRs to activate the AhR signal transduction pathway at moderate to high concentrations as assessed using both assays. AhR-dependent activation by BFRs may be due in part to contaminants present in commercial/technical mixtures. This was suggested by our comparative analysis of Firemaster BP-6 versus its primary component 2,2',4,4',5,5'-hexabromobiphenyl. Some technical mixtures of brominated flame-retardants contain brominated biphenyls, dioxins or dibenzofurans as contaminants. When tested in the CALUX assay these compounds were found to be equivalent to, or more active than their chlorinated analogues. Relative effective potency values were determined from dose response curves for these brominated HAHs.

Structure and ligand of a histone acetyltransferase bromodomain.

Histone acetylation is important in chromatin remodelling and gene activation. Nearly all known histone-acetyltransferase (HAT)-associated transcriptional co-activators contain bromodomains, which are approximately 110-amino-acid modules found in many chromatin-associated proteins. Despite the wide occurrence of these bromodomains, their three-dimensional structure and binding partners remain unknown. Here we report the solution structure of the bromodomain of the HAT co-activator P/CAF (p300/CBP-associated factor). The structure reveals an unusual left-handed up-and-down four-helix bundle. In addition, we show by a combination of structural and site-directed mutagenesis studies that bromodomains can interact specifically with acetylated lysine, making them the first known protein modules to do so. The nature of the recognition of acetyl-lysine by the P/CAF bromodomain is similar to that of acetyl-CoA by histone acetyltransferase. Thus, the bromodomain is functionally linked to the HAT activity of co-activators in the regulation of gene transcription.

Vanadium haloperoxidases.

The nature of the oxidized halogen intermediate in vanadium bromoperoxidase has recently been shown to depend on the nature of the organic substrate. For example, in the presence of indoles, vanadium bromoperoxidase does not release a freely diffusible oxidized halogen intermediate (such as HOBr+/-BR2+/-Br3-). Regioselective investigations are, therefore, now feasible.