Abstract
Five polybrominated oxydiphenol derivatives have been isolated from various Great Barrier Reef collections and one Fijian collection of the sponge Dysidea herbacea: 3,4',5,6,6'-hexabromo-2, 2'-oxydiphenol (11), 3,4',5,6,6'-pentabromo-2,2'-oxydiphenol (12), 3.4',5,6,6'-pentabromo-2,2'-oxydiphenol 1-methyl ether (13), 3,4,4',5,6'-pentabromo-2,2'-oxydiphenol 1,1'-dimethyl ether (14) and 3,4',5,6'-tetrabromo-2,2'-oxydiphenol 1'-methyl ether (15). The structure of the first member of this series is determined by a new method involving 13C spin-lattice relaxation data. The contributions of nearby hydrogens to quaternary carbon spin-lattice relaxation times are calculated for various possible structures and compared with the experimental data, leading to an unequivocal proof of structure. The structures of the remaining compounds in the series are established principally by analysis of 13C chemical shifts and 13C-1H coupling constants.
| Original language | English |
|---|---|
| Pages (from-to) | 2341-2349 |
| Number of pages | 9 |
| Journal | Tetrahedron |
| Volume | 37 |
| Issue number | 13 |
| DOIs | |
| Publication status | Published - 1981 |
| Externally published | Yes |
Cite this
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Polybrominated oxydiphenol derivatives from the sponge dysidea herbacea. Structure determination by analysis of 13C spin-lattice relaxation data for quaternary carbons and 13C-1H coupling constants. / Norton, Raymond S.; Croft, Kevin D.; Wells, Robert J.
In: Tetrahedron, Vol. 37, No. 13, 1981, p. 2341-2349.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - Polybrominated oxydiphenol derivatives from the sponge dysidea herbacea. Structure determination by analysis of 13C spin-lattice relaxation data for quaternary carbons and 13C-1H coupling constants
AU - Norton, Raymond S.
AU - Croft, Kevin D.
AU - Wells, Robert J.
PY - 1981
Y1 - 1981
N2 - Five polybrominated oxydiphenol derivatives have been isolated from various Great Barrier Reef collections and one Fijian collection of the sponge Dysidea herbacea: 3,4',5,6,6'-hexabromo-2, 2'-oxydiphenol (11), 3,4',5,6,6'-pentabromo-2,2'-oxydiphenol (12), 3.4',5,6,6'-pentabromo-2,2'-oxydiphenol 1-methyl ether (13), 3,4,4',5,6'-pentabromo-2,2'-oxydiphenol 1,1'-dimethyl ether (14) and 3,4',5,6'-tetrabromo-2,2'-oxydiphenol 1'-methyl ether (15). The structure of the first member of this series is determined by a new method involving 13C spin-lattice relaxation data. The contributions of nearby hydrogens to quaternary carbon spin-lattice relaxation times are calculated for various possible structures and compared with the experimental data, leading to an unequivocal proof of structure. The structures of the remaining compounds in the series are established principally by analysis of 13C chemical shifts and 13C-1H coupling constants.
AB - Five polybrominated oxydiphenol derivatives have been isolated from various Great Barrier Reef collections and one Fijian collection of the sponge Dysidea herbacea: 3,4',5,6,6'-hexabromo-2, 2'-oxydiphenol (11), 3,4',5,6,6'-pentabromo-2,2'-oxydiphenol (12), 3.4',5,6,6'-pentabromo-2,2'-oxydiphenol 1-methyl ether (13), 3,4,4',5,6'-pentabromo-2,2'-oxydiphenol 1,1'-dimethyl ether (14) and 3,4',5,6'-tetrabromo-2,2'-oxydiphenol 1'-methyl ether (15). The structure of the first member of this series is determined by a new method involving 13C spin-lattice relaxation data. The contributions of nearby hydrogens to quaternary carbon spin-lattice relaxation times are calculated for various possible structures and compared with the experimental data, leading to an unequivocal proof of structure. The structures of the remaining compounds in the series are established principally by analysis of 13C chemical shifts and 13C-1H coupling constants.
UR - http://www.scopus.com/inward/record.url?scp=0000561951&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)88887-6
DO - 10.1016/S0040-4020(01)88887-6
M3 - Article
AN - SCOPUS:0000561951
VL - 37
SP - 2341
EP - 2349
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 13
ER -