X-ray structural studies on organobromine and organochlorine compounds
Abstract
The structures of nine organic compounds containing bromine or chlorine were studied by single crystal X-ray diffraction. The compounds belong to two different classes of halogenated organics. Three of the compounds were polybrominated polycyclic ethers formed through transannular reactions during the treatment of two isomers of cyclododeca-1,5,9-triene with N-bromosuccinimide in methanol. These compounds were endo,endo-5,9-dibromo-cis-transoidcis-13-oxa-tricyclo[8.2.l.02.6]tridecane (I), endo,endo,exo-2,6,10-tribromo-exo-5-methoxy-13-oxa-trans-bicyclo[7.3.1]tridecane (II) and (E)-exo,endo-2,5,10-
tribromo-exo-6-methoxy-13-oxa-cis-bicyclo[7.3.1]tridec-4-ene (III). The remaining six compounds were polychlorinatied aromatics used as model compounds in environmental analyses: 1,2,3,4-tetrachlorodibenzo-p-dioxin (IV), pentachloromethoxy benzene (V), 2,2',3,4',5'-pentachloro-4-methoxybiphenyl (VI), 2,2',4,4',5',6-hexachloro-3-methoxybiphenyl (VII), bis(2,4-dichlorophenyl) ether (VIII) and 2,2',3,4,4',5'-hexachlorodiphenyl ether (IX).
All structures were solved by Direct Methods, but the procedure used for the three brominated polycyclic ethers differed from the normal one. These compounds were taken for structure analysis directly from the synthesis, with no other information available about their chemical composition except that provided by the synthesis. A qualitative procedure for estimating the chemical composition from experimental crystallographic data and information about the synthesis is described and is applied as an expedient to structure solution for the three compositionally indeterminate polycyclic bromo compounds.
Main Author
Format
Theses
Doctoral thesis
Published
1990
Series
ISBN
978-952-86-0103-6
The permanent address of the publication
https://urn.fi/URN:ISBN:978-952-86-0103-6Use this for linking
Language
English
Published in
Annales Academiae scientiarum Fennicae
Contains publications
- Artikkeli I: Rissanen, K., Valkonen, J., & Haufe, G. (1987). endo,endo-5,9-Dibromo-cis-transoid-cis-13-oxatricyclo-[8.2.1.02,6]tridecane. Acta Crystallographica, C43(10), 1961-1964. DOI: 10.1107/S0108270187089455
- Artikkeli II: Rissanen, K. & Haufe, G. (1988). endo,endo,exo-2,6, 1 0-Tribromo-exo-5-methoxy-l 3-oxa-trans-bicyclo[7.3. l]tridecane. Acta Crystallica, C44, 1803-1805. DOI: 10.1107/S0108270188007012
- Artikkeli III: Rissanen, K. & Haufe, G. (1989). ( E)-exo ,endo-2,5,1 0-Tribromo-exo-6-methoxy-13-oxa-cis-bicyclo[7 .3.1 ]tridec-4-ene. Acta Crystallica, C45, 1617-1619. DOI: 10.1107/S0108270189003252
- Artikkeli IV: Rissanen, K., Valkonen, J., & Tarhanen, J. (1987). 1,2,3,4-Tetrachlorodi-benzo-p-dioxin. Acta Crystallographica, C43(3), 488-490. DOI: 10.1107/S0108270187095283
- Artikkeli V: Rissanen, K., Valkonen, J., & Knuutinen, J. (1987). Conformational Effects in Methoxybenzenes Caused by Ortho Disubstitution. I. Pentachloro-methoxybenzene. Acta Crystallographica, C43, 1966-1968. DOI: 10.1107/S0108270187089431
- Artikkeli VI: Rissanen, K., Valkonen, J. and Mannila, B. (1988). Structures of Chlorinated Methoxybiphenyls. I. 2,2',3,4',5' -Pentachloro-4-methoxybiphenyl. Acta Crystallica, C44, 682-684. DOI: 10.1107/S0108270187011521
- Artikkeli VII: Rissanen, K., Valkonen, J. and Mannila, B. (1988). Structures of Chlorinated Methoxybiphenyls. II. 2,2' ,4,4' ,5' ,6-Hexachloro-3-methoxybiphenyl. Acta Cryst., C44, 684-686. DOI: 10.1107/S0108270187011533
- Artikkeli VIII: Rissanen, K., Valkonen, J. and Virkki, L. (1988). Bis(2,4-dichlorophenyl) Ether. Acta Cryst., C44, 1644-1646. DOI: 10.1107/S0108270188005839
- Artikkeli IX: Rissanen, K. and Virkki, L. (1989). 2,2' ,3,4,4' ,5' -Hexachlorodiphenyl Ether. Acta Cryst., C45, 1408-1410, DOI: 10.1107/S0108270189001368