The reaction of N,N-spiro bridged octachlorobis(cyclotriphosphazene) with 1,3-propanediol: Comparison with 1,2-ethanediol

Abstract

The reaction of the N,N-spiro bridged octachlorobis(cyclotriphosphazene), {N3P3Cl4[br-N (CH2)(5)CH3](2)N3P3Cl4) (1), in three stoichiometries (1:0.7, 1:2 and 1:4) with the disodium salt of 1,3-propanediol in THF at room temperature produced seven products, whose structures have been characterized by elemental analysis, mass spectrometry, H-1 and P-31 NMR spectroscopy; also the crystal structures of 6 and 8 were determined by X-ray crystallography. The reactions gave a mixture of rearranged derivatives (2, 4 and 5) in which the central four membered cyclophosphazane ring transformed into a six-membered monocyclophosphazene ring, as well as the normal substituted derivatives (3, 6-8). In addition, the results of all the reactions were compared with previous work on the reactions of the starting compound 1 with the disodium derivative of 1,2-ethanediol, in the same mole ratios and in the same solvent, THF. (C) 2016 Elsevier Ltd. All rights reserved.