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

Abstract

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.