Intramolecular versus intermolecular oxidative couplings of ester tethered di-aryl ethers

Taylor, SR; Ung, AT; Pyne, SG; Skelton, BW; White, AH

Intramolecular versus intermolecular oxidative couplings of ester tethered di-aryl ethers

Taylor, SR Ung, AT

Pyne, SG Skelton, BW White, AH

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Publication Type:: Journal Article
Citation:: Tetrahedron, 2007, 63 (46), pp. 11377 - 11385
Issue Date:: 2007-11-12

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Field	Value	Language
dc.contributor.author	Taylor, SR	en_US
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.contributor.author	Pyne, SG	en_US
dc.contributor.author	Skelton, BW	en_US
dc.contributor.author	White, AH	en_US
dc.date.issued	2007-11-12	en_US
dc.identifier.citation	Tetrahedron, 2007, 63 (46), pp. 11377 - 11385	en_US
dc.identifier.issn	0040-4020	en_US
dc.identifier.uri	http://hdl.handle.net/10453/8464
dc.description.abstract	The oxidative cyclization of 3,4-dimethoxyphenyl 3,4-dimethoxyphenylacetate, through intramolecular biphenyl bond formation, was successful and gave the target seven-membered lactone in good yield (85-86%). All other ester substrates gave biphenyl products or their further oxidized products via intermolecular coupling of their radical cation intermediate with the neutral substrate. It appears that matching of the oxidation potentials and nucleophilicity of the two phenyl rings, the positioning of the ring substituents and the ease of E to Z isomerization about the ester C-O bond are important factors contributing to these product outcomes. Crown Copyright © 2007.	en_US
dc.relation.ispartof	Tetrahedron	en_US
dc.relation.isbasedon	10.1016/j.tet.2007.08.082	en_US
dc.subject.classification	Organic Chemistry	en_US
dc.title	Intramolecular versus intermolecular oxidative couplings of ester tethered di-aryl ethers	en_US
dc.type	Journal Article
utslib.citation.volume	46	en_US
utslib.citation.volume	63	en_US
utslib.for	0305 Organic Chemistry	en_US
utslib.for	0304 Medicinal and Biomolecular Chemistry	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access
pubs.issue	46	en_US
pubs.publication-status	Published	en_US
pubs.volume	63	en_US

Abstract:

The oxidative cyclization of 3,4-dimethoxyphenyl 3,4-dimethoxyphenylacetate, through intramolecular biphenyl bond formation, was successful and gave the target seven-membered lactone in good yield (85-86%). All other ester substrates gave biphenyl products or their further oxidized products via intermolecular coupling of their radical cation intermediate with the neutral substrate. It appears that matching of the oxidation potentials and nucleophilicity of the two phenyl rings, the positioning of the ring substituents and the ease of E to Z isomerization about the ester C-O bond are important factors contributing to these product outcomes. Crown Copyright © 2007.

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http://hdl.handle.net/10453/8464