Issue 10, 2006

The structural and stereogenic properties of pentaerythritoxy-bridged cyclotriphosphazene derivatives: spirospiro, spiroansa and ansaansa isomers

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 spirospiro, spiroansa and ansaansa. The structures and stereogenic properties of the products were characterised by X-ray crystallography and 31P NMR spectroscopy on addition of the chiral solvating agent, (S)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol. Molecules with spirospiro and spiroansa bridged gem-disubstituted cyclophosphazenes [R = Ph, NHBut or (OCH2CF2CF2CH2O)0.5] are found to be chiral and exist as racemates. Molecules with ansaansa 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.

Graphical abstract: The structural and stereogenic properties of pentaerythritoxy-bridged cyclotriphosphazene derivatives: spiro–spiro, spiro–ansa and ansa–ansa isomers

Supplementary files

Article information

Article type
Paper
Submitted
13 Sep 2005
Accepted
14 Oct 2005
First published
18 Nov 2005

Dalton Trans., 2006, 1302-1312

The structural and stereogenic properties of pentaerythritoxy-bridged cyclotriphosphazene derivatives: spirospiro, spiroansa and ansaansa isomers

S. J. Coles, D. B. Davies, R. J. Eaton, M. B. Hursthouse, A. Kılıç, R. A. Shaw and A. Uslu, Dalton Trans., 2006, 1302 DOI: 10.1039/B512854D

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