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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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.
|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
|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)
|RDF:||RDF+N-Triples, RDF+N3, RDF+XML, Browse.|
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