title: Preparation and X-ray structural characterization of further stereoisomers of 1,2,5,6,9,10-hexabromocyclododecane.
abstract: Technical 1,2,5,6,9,10-hexabromocyclododecane (HBCD) consists largely of three diastereomers (α-, β-, and γ-HBCD) produced by the trans addition of bromine to cis,trans,trans-cyclododeca-1,5,9-triene (CDT). However, another seven diastereomers are theoretically possible and may be produced by trans addition of bromine across the double bonds of the other three isomers of 1,5,9-CDT. There are indications that small amounts of the minor HBCD isomers may be present in commercial HBCD mixtures or in products containing this brominated flame retardant (BFR). Such minor components may indeed derive from traces of other 1,5,9-CDTs in the cis, trans, trans starting material, however their formation may also be possible through isomerizations during the processing of this BFR or by bioisomerization subsequent to its release into the environment. Two of the seven additional diastereomers (δ- and ε-HBCD) were synthesized previously from trans,trans,trans-CDT. We now report the preparation of the remaining five diastereomers, ζ-, η-, and θ-HBCD from cis,cis,trans-CDT and ι- and κ-HBCD from cis,cis,cis-CDT, and their characterization by (1)H NMR spectroscopy and X-ray crystallography. The availability of these further diastereomers of HBCDshould aid in determining if the minor isomers are present in commercial samples of this BFR, in products containing HBCDs, or in environmental samples. We have also carried out an X-ray crystal structure determination on ε-HBCD, so that crystal structures are now available for all 10 HBCD diastereomers.
authors: Wellington Laboratories, Research Division, Guelph, ON, Canada N1G 3M5. nicole@well-labs.com
authors: Nicole
authors: N
authors: Riddell
authors: Roland
authors: R
authors: Becker
authors: Brock
authors: B
authors: Chittim
authors: Franziska
authors: F
authors: Emmerling
authors: Robert
authors: R
authors: Köppen
authors: Alan
authors: A
authors: Lough
authors: Alan
authors: A
authors: McAlees
authors: Robert
authors: R
authors: McCrindle
mesh_terms: D002853:Chromatography, Liquid; D018360:Crystallography, X-Ray; D004785:Environmental Pollutants / Q000737:chemistry*; D005411:Flame Retardants; D054879:Halogenation; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure
chemical_list: D004785:Environmental Pollutants; D005411:Flame Retardants; D006842:Hydrocarbons, Brominated; C089796:hexabromocyclododecane