Document Detail

Preparation and X-ray structural characterization of further stereoisomers of 1,2,5,6,9,10-hexabromocyclododecane.
MedLine Citation:
PMID:  21724224     Owner:  NLM     Status:  Publisher    
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.
Nicole Riddell; Roland Becker; Brock Chittim; Franziska Emmerling; Robert Köppen; Alan Lough; Alan McAlees; Robert McCrindle
Related Documents :
21588424 - (2-methyl-phen-yl)(phen-yl)methanol.
21754824 - 9-(3,4-dimeth-oxy-phen-yl)-3,4,5,6,7,9-hexa-hydroxanthene-1,8(2h)-dione.
11674434 - Effect of angle strain in conjugated cycloalkenylidenes. singlet-triplet splitting of c...
18640054 - Low-temperature thermolysis behavior of tetramethyl- and tetraethyldistibines.
25249874 - Crystal structure of 1,1-di-acetyl-ferrocene dihydrazone.
14562314 - Hydrogenation versus transfer hydrogenation of ketones: two established ruthenium syste...
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-7-1
Journal Detail:
Title:  Chemosphere     Volume:  -     ISSN:  1879-1298     ISO Abbreviation:  -     Publication Date:  2011 Jul 
Date Detail:
Created Date:  2011-7-4     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0320657     Medline TA:  Chemosphere     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 Elsevier Ltd. All rights reserved.
Wellington Laboratories, Research Division, Guelph, ON, Canada N1G 3M5.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Previous Document:  Sediment analysis to support the recent glacial origin of DDT pollution in Lake Iseo (Northern Italy...
Next Document:  Novel metabolic pathways of organochlorine pesticides dieldrin and aldrin by the white rot fungi of ...