The synthesis of a novel, heterocyclic-telechelic polymer, -oxetanyl-telechelic poly(3-nitratomethyl-3-methyl oxetane), is described. Infra-red spectroscopy (IR), gel permeation chromatography (GPC) and nuclear magnetic resonance (NMR) spectroscopy have been used to confirm the successful synthesis, demonstrating the presence of the telechelic-oxetanyl moieties. Synthesis of the terminal functionalities has been achieved via displacement of nitrato groups, in a manner similar to that employed with other leaving groups such as azido, bromo and nitro, initiated by nucleophiles. In the present case, displacement occurs on the ends of a nitratofunctionalised polymer driven by the formation of sodium nitrate, which is supported by the polar aprotic solvent, N,N-dimethyl formamide. The formation of an alkoxide at the polymer chain ends is favoured and allows internal backbiting to the nearest carbon bearing the nitrato group, intrinsically in an SN1 reaction, leading to oxetanyl functionalisation. The telechelic-oxetanyl moieties have the potential to be cross-linked by chemical (e.g. acidic), or radiative (e.g. U.V.) curing methods without the use of high temperatures, usually below 100 o C. This type of material was designed for future use as a contraband simulant, whereby it would form the predominant constituent of elastomeric composites comprising rubbery polymer with small quantities of solids, typically crystals of contraband substances, such as explosives or narcotics. This method also provides an alternative approach to ringclosure and synthesis of heterocycles.
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