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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, N(3)P(3)Cl(6) (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 N(3)P(3)Cl(4)[OCH(2)(CF(2))(4)CH(2)O](3); the single-bridged compound N(3)P(3)Cl(5)[OCH(2)(CF(2))(4)CH(2)O]N(3)P(3)Cl(5) (4), two double-bridged compounds N(3)P(3)Cl(4)(OCH(2)(CF(2))(4)CH(2)O)(2)N(3)P(3)Cl(4), (5-anti, 5-syn) and the triple-bridged compound N(3)P(3)Cl(3)(OCH(2)(CF(2))(4)CH(2)O)(3)N(3)P(3)Cl(3) (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 tripie-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. (C) 2009 Elsevier Ltd. All rights reserved.
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, N(3)P(3)Cl(6) (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 N(3)P(3)Cl(4)[OCH(2)(CF(2))(4)CH(2)O](3); the single-bridged compound N(3)P(3)Cl(5)[OCH(2)(CF(2))(4)CH(2)O]N(3)P(3)Cl(5) (4), two double-bridged compounds N(3)P(3)Cl(4)(OCH(2)(CF(2))(4)CH(2)O)(2)N(3)P(3)Cl(4), (5-anti, 5-syn) and the triple-bridged compound N(3)P(3)Cl(3)(OCH(2)(CF(2))(4)CH(2)O)(3)N(3)P(3)Cl(3) (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 tripie-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. (C) 2009 Elsevier Ltd. All rights reserved.

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

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Local EPrints ID: 346362
URI: https://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: 06 Jun 2018 12:54

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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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