Amino alcohol based cyclotriphosphazenes: Effects of chain length and base factor on product diversity

The reactions of hexachlorocyclotriphosphazene with amino alcohols with different chain lengths were investigated by using three different bases. [Display omitted] •The reactions of trimer (1) with two different amino alcohols (2a and 2b) were investigated.•The product formation was discussed in terms of chain length of amino alcohol and the role of base.•A possible reaction mechanism for the progress of the reactions has been proposed.•Crystal parameters of mono spiro cyclotriphosphazene derivatives were evaluated comparatively. The effects of chain length and base on product diversity in the reactions of hexachlorocyclotriphosphazene, N3P3Cl6 (1) with amino alcohols (2a and 2b) have been reported. In this sense, two different amino alcohols (2a and 2b) and three different base solutions (Et3N, NaH and amino alcohol itself) were selected. All reactions were performed at 1:1 mol ratio in THF solvent and under argon atmosphere. These reactions led to formation of open chain (3a, 3b and 7b) and spiro (4a-6a and 4b) compounds. The isolated compounds (3a-5a, 3b, 4b and 7b) have been characterized by elemental analysis, MALDI-TOF mass spectrometry, 1H, and 31P NMR spectroscopy. The molecular and crystal structures of 4a, 5a and 4b were illuminated by X-Ray crystallography. The product formations and their amounts were discussed in terms of two different aspects: chain length of the nucleophile and the role of base. In addition, the product varieties in the reactions of hexachlorocyclotriphosphazene with diols, diamines and amino alcohols were mentioned.