Simon J. Coles
A structural and mechanistic investigation of the mono-O-phenylation of diols with BiPh3(OAc)2
Coles, Simon J.; Costello, James F.; Hursthouse, Michael B.; Smith, Stephen
Abstract
The mono-O-phenylation of enantiomerically pure pinanediol 2 using BiPh3(OAc)2 1 and the biphenyl-2,2′-ylenephenylbismuth analogue 9 has been investigated. It is postulated that reductive elimination at the trigonal bipyramidal bismuth (V) centre of 1 upon exposure to ambient light affects the transfer of an apical phenyl ligand to the least sterically encumbered hydroxyl group of the diol, affording the monophenyl ether in good yield. SbPh3(OAc)2 fails to undergo reductive elimination, affording the stable diolate 6 instead. The X-ray crystal structure of 6 provides a reasonable model for the intermediate of the bismuth mono-O-phenylation, and suggests further studies with bismuth complexes such as 9 possessing intramolecularly tethered ligands incapable of facilitating the mono-O-phenylation reaction. The discussions are supported by X-ray crystallographic correlations, and calculations indicate that (M)-(-)-6 adopts the lowest energy conformational diastereoisomer. © 2002 Elsevier Science B.V. All rights reserved.
Journal Article Type | Article |
---|---|
Publication Date | Nov 15, 2002 |
Journal | Journal of Organometallic Chemistry |
Print ISSN | 0022-328X |
Publisher | Elsevier |
Peer Reviewed | Peer Reviewed |
Volume | 662 |
Issue | 1-2 |
Pages | 98-104 |
DOI | https://doi.org/10.1016/S0022-328X%2802%2901895-8 |
Keywords | mono-O-phenylation, organobismuth, propellers |
Public URL | https://uwe-repository.worktribe.com/output/1075664 |
Publisher URL | http://dx.doi.org/10.1016/S0022-328X(02)01895-8 |
You might also like
Book review: Whiteness and White Privilege in Psychotherapy
(2016)
Journal Article
The Development of Novel Fuel Dehydrating Icing Inhibitors
(2013)
Journal Article
Dual Action Additives for Jet A-1: Fuel Dehydrating Icing Inhibitors
(2016)
Journal Article
Downloadable Citations
About UWE Bristol Research Repository
Administrator e-mail: repository@uwe.ac.uk
This application uses the following open-source libraries:
SheetJS Community Edition
Apache License Version 2.0 (http://www.apache.org/licenses/)
PDF.js
Apache License Version 2.0 (http://www.apache.org/licenses/)
Font Awesome
SIL OFL 1.1 (http://scripts.sil.org/OFL)
MIT License (http://opensource.org/licenses/mit-license.html)
CC BY 3.0 ( http://creativecommons.org/licenses/by/3.0/)
Powered by Worktribe © 2024
Advanced Search