Abstract
The nucleophilic substitution reactions of mono- and bis-spiro-2,2′ -dioxybiphenyl cyclotriphosphazenes (3 and 4) with cyclopropanemethylamine (5) and aniline (6) were performed in the presence of trimethylamine in THF. Five novel cyclopropanemethylamino- and anilino-substituted spiro-2,2′ -dioxybiphenyl cyclotriphosphazene derivatives (7–11) were obtained from these reactions. The molecular structures of the new cyclotriphosphazene derivatives (7–11) were characterized by elemental analysis, MALDI-TOF MS, FT-IR, and NMR ( 31 P and 1 H) spectroscopies. The structure of the spiro-(2,2′ -dioxybiphenyl)-bis-(anilino)-cyclotriphosphazene (11) was also determined by single-crystal X-ray crystallography.
Highlights
Among the inorganic heterocyclic rings, cyclotriphosphazenes have attracted interest due to their use as scaffolds for the preparation of a wide variety of functional and speciality materials [1,2,3,4,5]
The cyclotriphosphazene core is renowned for the extreme robustness of its phosphorus-nitrogen backbone and 6 very active phosphorouschlorine bonds, which enable nucleophilic substitution reactions with mono and difunctional reagents [6,7,8,9,10]
Due to the role of the cyclotriphosphazene ring in the design of new molecules and the advantages of functional groups containing nitrogen atoms, this study focused on the reactions of monoand bis-spiro-2,2 ′ -dioxybiphenyl cyclotriphosphazenes with new reagents, such as cyclopropanemethylamine and aniline
Summary
Among the inorganic heterocyclic rings, cyclotriphosphazenes have attracted interest due to their use as scaffolds for the preparation of a wide variety of functional and speciality materials [1,2,3,4,5]. Other advantages of the cyclotriphosphazene scaffold are the possibility to control the reaction pathways in substitution reactions and obtain new derivatives that have different properties depending on the characteristics of the functional groups [3,4,9,10]. Due to the role of the cyclotriphosphazene ring in the design of new molecules and the advantages of functional groups containing nitrogen atoms, this study focused on the reactions of monoand bis-spiro-2,2 ′ -dioxybiphenyl cyclotriphosphazenes with new reagents, such as cyclopropanemethylamine and aniline. The newly cyclopropanemethylamino- and anilino-substituted spiro-2,2 ′ -dioxybiphenyl cyclotriphosphazene derivatives (7–11) were designed and synthesized (Scheme). NMR spectra ( 1 H and 31 P) were recorded for the newly synthesized compounds in CDCl 3 solutions on a Varian INOVA 500 MHz spectrometer (Palo Alto, CA, USA).
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