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

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).

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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Contributors

Author: Simon J. Coles

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