The structural and stereogenic properties of pentaerythritoxy-bridged cyclotriphosphazene derivatives: spiro-spiro, spiro-ansa and ansa-ansa isomers
Coles, Simon J., Davies, David B., Eaton, Robert J., Hursthouse, Michael B., Kiliç, Adem, Shaw, Robert A. and Uslu, Aylin (2006) The structural and stereogenic properties of pentaerythritoxy-bridged cyclotriphosphazene derivatives: spiro-spiro, spiro-ansa and ansa-ansa isomers. Dalton Transactions, (10), 1302-1312. (doi:10.1039/b512854d).
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Description/Abstract
Reactions of pentaerythritol with hexachlorocyclotriphosphazene, N3P3Cl6, and gem-disubstituted cyclotriphosphazene derivatives, N3P3Cl4R2 [R = Ph, NHBut or (OCH2CF2CF2CH2O)(0.5)] gave a series of pentaerythritol-bridged derivatives linked spiro-spiro, spiro-ansa and ansa-ansa. The structures and stereogenic properties of the products were characterised by X-ray crystallography and P-31 NMR spectroscopy on addition of the chiral solvating agent, (S)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol. Molecules with spiro-spiro and spiro-ansa bridged gem-disubstituted cyclophosphazenes [R = Ph, NHBut or (OCH2CF2CF2CH2O) 0.5] are found to be chiral and exist as racemates. Molecules with ansa-ansa bridged cyclophosphazenes [R = Cl or (OCH2CF2CF2CH2O) 0.5] have been characterised for the first time and are shown to have meso configurations. Analysis of crystal structure data shows that the six-membered chair form of the spiro rings and the eight-membered boat-chair form of the ansa rings in the bridged compounds are similar to analogous spiro and ansa exocyclic ring conformations of 1,3-propanedioxy-derivatives of cyclophosphazenes.
| Item Type: | Article |
|---|---|
| ISSNs: | 1477-9226 (print) |
| Related URLs: | |
| Keywords: | phosphorus-nitrogen-compounds, ray crystal-structures, substituent constants, n3p3cl22 derivatives, phosphazene chemistry, nmr-spectra, 1st example, basicity, hexachlorocyclotriphosphazatriene, cyclophosphazenes |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 44410 |
| Date Deposited: | 01 Mar 2007 |
| Last Modified: | 01 Jun 2011 02:24 |
| Contributors: | Coles, Simon J. (Author) Davies, David B. (Author) Eaton, Robert J. (Author) Hursthouse, Michael B. (Author) Kiliç, Adem (Author) Shaw, Robert A. (Author) Uslu, Aylin (Author) |
| Date: | 2006 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/44410 |
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