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Single-, double- and triple-bridged derivatives of cyclotriphosphazenes with an octafluorohexane-1,6-diol

Single-, double- and triple-bridged derivatives of cyclotriphosphazenes with an octafluorohexane-1,6-diol
Single-, double- and triple-bridged derivatives of cyclotriphosphazenes with an octafluorohexane-1,6-diol
Reaction of hexachlorocyclotriphosphazene, N3P3Cl6 (1), with the sodium derivative of the fluorinated diol, 2,2,3,3,4,4,5,5-octafluorohexane-1,6-diol, (2), in THF solution at room temperature afforded five products, whose structures have been characterised by (1)H, (19)F and (31)P NMR spectroscopy: the mono-ansa compound N3P3Cl4[OCH2(CF2)4CH2O]3; the single-bridged compound N3P3Cl5)[OCH2(CF2)4CH2O]N3P3Cl5 (4), two double-bridged compounds N3P3Cl4(OCH2(CF2)4CH2O)2N3P3Cl4, (5-anti, 5-syn) and the triple-bridged compound N3P3Cl3(OCH2(CF2)4CH2O)3N3P3Cl3 (6). X-ray crystallographic studies confirmed the structures of the ansa compound (3), the double-bridged compound (5-anti) and the first example of a triple-bridged cyclotriphosphazene derivative (6). The results were also compared with those for reactions of (1) with analogous fluorinated shorter diols (1,4-butane- and 1,5-pentane-diols). It is found that on increasing the chain length of the diol, there is a decrease in the relative proportion of intramolecular reactions giving spiro and ansa derivatives and an increase in the amount of bridged cyclophosphazene derivatives via intermolecular reactions.
0277-5387
3593-3599
Beşli, Serap
63ec1cf4-d0d6-4982-9e0a-c632f1f98d08
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Davies, David B.
675b90e6-0c3c-468b-9996-326220517cc6
Erkovan, Ayşen O.
9bde62db-83b8-402d-abbd-70adea25bcd9
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Kılıç, Adem
565a42ec-2d18-4142-8b37-bb74b244b2f5
Beşli, Serap
63ec1cf4-d0d6-4982-9e0a-c632f1f98d08
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Davies, David B.
675b90e6-0c3c-468b-9996-326220517cc6
Erkovan, Ayşen O.
9bde62db-83b8-402d-abbd-70adea25bcd9
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Kılıç, Adem
565a42ec-2d18-4142-8b37-bb74b244b2f5

Beşli, Serap, Coles, Simon J., Davies, David B., Erkovan, Ayşen O., Hursthouse, Michael B. and Kılıç, Adem (2009) Single-, double- and triple-bridged derivatives of cyclotriphosphazenes with an octafluorohexane-1,6-diol. Polyhedron, 28 (16), 3593-3599. (doi:10.1016/j.poly.2009.07.042).

Record type: Article

Abstract

Reaction of hexachlorocyclotriphosphazene, N3P3Cl6 (1), with the sodium derivative of the fluorinated diol, 2,2,3,3,4,4,5,5-octafluorohexane-1,6-diol, (2), in THF solution at room temperature afforded five products, whose structures have been characterised by (1)H, (19)F and (31)P NMR spectroscopy: the mono-ansa compound N3P3Cl4[OCH2(CF2)4CH2O]3; the single-bridged compound N3P3Cl5)[OCH2(CF2)4CH2O]N3P3Cl5 (4), two double-bridged compounds N3P3Cl4(OCH2(CF2)4CH2O)2N3P3Cl4, (5-anti, 5-syn) and the triple-bridged compound N3P3Cl3(OCH2(CF2)4CH2O)3N3P3Cl3 (6). X-ray crystallographic studies confirmed the structures of the ansa compound (3), the double-bridged compound (5-anti) and the first example of a triple-bridged cyclotriphosphazene derivative (6). The results were also compared with those for reactions of (1) with analogous fluorinated shorter diols (1,4-butane- and 1,5-pentane-diols). It is found that on increasing the chain length of the diol, there is a decrease in the relative proportion of intramolecular reactions giving spiro and ansa derivatives and an increase in the amount of bridged cyclophosphazene derivatives via intermolecular reactions.

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More information

Published date: 3 November 2009
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 346362
URI: http://eprints.soton.ac.uk/id/eprint/346362
ISSN: 0277-5387
PURE UUID: 09929060-d7ea-4000-bf68-2eba3193daad
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 20 Dec 2012 15:23
Last modified: 15 Mar 2024 03:01

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Contributors

Author: Serap Beşli
Author: Simon J. Coles ORCID iD
Author: David B. Davies
Author: Ayşen O. Erkovan
Author: Adem Kılıç

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