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Stereoisomerism in pentaerythritol-bridged cyclotriphosphazene tri-spiranes: spiro and ansa 1,3-propanediyldioxy disubstituted derivatives

Stereoisomerism in pentaerythritol-bridged cyclotriphosphazene tri-spiranes: spiro and ansa 1,3-propanediyldioxy disubstituted derivatives
Stereoisomerism in pentaerythritol-bridged cyclotriphosphazene tri-spiranes: spiro and ansa 1,3-propanediyldioxy disubstituted derivatives
Four isomeric products were isolated and purified from the reaction of 1,3-propanediol with the tri-spirane cyclophosphazene-organophosphate compound 1: viz. the di-monospiro (2a), di-monoansa (2b) and two monospiro-monoansa derivatives (2c and 2d). It is shown by P-31 NMR spectroscopy on addition of a chiral solvating agent (CSA) that both the di-monospiro 2a and di-monoansa 2b derivatives are racemates, as expected, whereas no splitting of NMR signals occurred on addition of CSA to solutions of 2c and 2d. It is found by X-ray crystallography that the two monospiro-monoansa spirane derivatives, 2c and 2d, are meso diastereoisomers, which represent a new case of the stereochemistry of bis(disubstituted) cyclophosphazene derivatives of 1. It is also observed from the P-31 NMR spectrum of the reaction mixture, supported by the yields of pure compounds, that formation of a spiro group is about 4.5 times more likely than that of an ansa moiety under the conditions of the reaction.
cyclotriphosphazene derivatives, trispiranes phosphorus-nitrogen compounds, cyclophosphazene derivatives, hexachlorocyclotriphosphazatriene, substitution, spectra
1434-1948
1042-1047
Uslu, Aylin
95af2437-3473-4022-8070-ad7d36524a87
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Davies, David B.
675b90e6-0c3c-468b-9996-326220517cc6
Eaton, Robert J.
e274676b-0499-47e1-8dbb-8d1ed908cdea
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Kiliç, Adem
53892b58-c3f9-4894-bdf9-6be70ab7611e
Shaw, Robert A.
fa783606-bfac-44c6-8371-7186eba65c3f
Uslu, Aylin
95af2437-3473-4022-8070-ad7d36524a87
Coles, Simon J.
65bb28e4-4917-43f5-a770-a00017d6783f
Davies, David B.
675b90e6-0c3c-468b-9996-326220517cc6
Eaton, Robert J.
e274676b-0499-47e1-8dbb-8d1ed908cdea
Hursthouse, Michael B.
a65b4d35-2ea0-47e7-938a-d744f4d9ba28
Kiliç, Adem
53892b58-c3f9-4894-bdf9-6be70ab7611e
Shaw, Robert A.
fa783606-bfac-44c6-8371-7186eba65c3f

Uslu, Aylin, Coles, Simon J., Davies, David B., Eaton, Robert J., Hursthouse, Michael B., Kiliç, Adem and Shaw, Robert A. (2005) Stereoisomerism in pentaerythritol-bridged cyclotriphosphazene tri-spiranes: spiro and ansa 1,3-propanediyldioxy disubstituted derivatives. European Journal of Inorganic Chemistry, (6), 1042-1047. (doi:10.1002/ejic.200400796).

Record type: Article

Abstract

Four isomeric products were isolated and purified from the reaction of 1,3-propanediol with the tri-spirane cyclophosphazene-organophosphate compound 1: viz. the di-monospiro (2a), di-monoansa (2b) and two monospiro-monoansa derivatives (2c and 2d). It is shown by P-31 NMR spectroscopy on addition of a chiral solvating agent (CSA) that both the di-monospiro 2a and di-monoansa 2b derivatives are racemates, as expected, whereas no splitting of NMR signals occurred on addition of CSA to solutions of 2c and 2d. It is found by X-ray crystallography that the two monospiro-monoansa spirane derivatives, 2c and 2d, are meso diastereoisomers, which represent a new case of the stereochemistry of bis(disubstituted) cyclophosphazene derivatives of 1. It is also observed from the P-31 NMR spectrum of the reaction mixture, supported by the yields of pure compounds, that formation of a spiro group is about 4.5 times more likely than that of an ansa moiety under the conditions of the reaction.

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More information

Published date: 18 March 2005
Keywords: cyclotriphosphazene derivatives, trispiranes phosphorus-nitrogen compounds, cyclophosphazene derivatives, hexachlorocyclotriphosphazatriene, substitution, spectra

Identifiers

Local EPrints ID: 20920
URI: http://eprints.soton.ac.uk/id/eprint/20920
ISSN: 1434-1948
PURE UUID: 8e865970-210c-41aa-a757-0eee302c54a3

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Date deposited: 01 Mar 2006
Last modified: 15 Jul 2019 19:25

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Contributors

Author: Aylin Uslu
Author: Simon J. Coles
Author: David B. Davies
Author: Robert J. Eaton
Author: Michael B. Hursthouse
Author: Adem Kiliç
Author: Robert A. Shaw

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