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

Raymond S. Norton, Kevin D. Croft, Robert J. Wells

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62 Citations (Scopus)

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 languageEnglish
Pages (from-to)2341-2349
Number of pages9
JournalTetrahedron
Volume37
Issue number13
DOIs
Publication statusPublished - 1981
Externally publishedYes

Cite this

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title = "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",
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.",
author = "Norton, {Raymond S.} and Croft, {Kevin D.} and Wells, {Robert J.}",
year = "1981",
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language = "English",
volume = "37",
pages = "2341--2349",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "13",

}

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 journalArticleResearchpeer-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

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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.

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