Issue 19, 2011
From the journal:

Dalton Transactions

Bridged cyclophosphazenes resulting from deprotonation reactions of cyclotriphophazenes bearing a P–NH group†

Serap Beşli,*a   Simon J. Coles,b   David B. Davies,c   Adem Kılıça  and  Robert A. Shawc  

* Corresponding authors

a Department of Chemistry, Gebze Institute of Technology, Gebze, Turkey
E-mail: besli@gyte.edu.tr
Fax: +90 2626053101
Tel: +90 2626053120

b Department of Chemistry, University of Southampton, Highfield, Southampton, UK

c School of Biological and Chemical Sciences, Birkbeck College (University of London), Malet Street, London, UK

Abstract

Cyclotriphosphazene derivatives containing a P–NHR group in the side-chain react in the presence of a strong base to form stable intermolecular bridged products. Reaction of sodium hydride with mono-spiro cyclophosphazene derivatives having a P–NH group, N3P3Cl4[O(CH2)3NH], (1a) or N3P3Cl4[CH3N(CH2)3NH], (1b) leads to formation of bis-cyclophosphazenes bridged with an eight-membered cyclophosphazene ring in an ansa arrangement (2a, 2b) whereas reaction of sodium hydride with mono-amino cyclophosphazene derivatives [N3P3Cl5(NHR), R = n-hexyl, 3a; i-Pr, 3b; Ph, 3c] give bis-cyclophosphazenes bridged with a four-membered cyclophosphazane ring in a spiro arrangement (4a–c). In the latter reaction P–O–P bridged compounds (5a–c) were also obtained as a result of hydrolysis reactions associated with the amount of moisture in the solvent tetrahydrofuran. In addition, it was found that reaction of a mixture of cyclotriphosphazene with either mono spiro compound, (1a) or (1b), in the presence of sodium hydride lead to formation of the first examples of asymmetrically-bridged cyclophosphazenes (6a–b).

Graphical abstract: Bridged cyclophosphazenes resulting from deprotonation reactions of cyclotriphophazenes bearing a P–NH group

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Article information

DOI
https://doi.org/10.1039/C1DT10073D
Article type
Paper
Submitted
14 Jan 2011
Accepted
16 Mar 2011
First published
07 Apr 2011

Dalton Trans., 2011,40, 5307-5315

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Bridged cyclophosphazenes resulting from deprotonation reactions of cyclotriphophazenes bearing a P–NH group

S. Beşli, S. J. Coles, D. B. Davies, A. Kılıç and R. A. Shaw, Dalton Trans., 2011, 40, 5307 DOI: 10.1039/C1DT10073D

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