Melem- and melamine-derived iminophosphoranes?

New Journal of Chemistry Pub Date: 2010-05-18 DOI: 10.1039/B9NJ00621D

Abstract

Iminophosphorane derivatives of s-triazine and tri-s-triazine, C3N3(N[double bond, length as m-dash]PCl3)3 (1), [H2C3N3NH2(N[double bond, length as m-dash]PPh3)2]Br2 (2), [HC3N3NH2(N[double bond, length as m-dash]PPh3)2]Br (3), C6N7(N[double bond, length as m-dash]PCl3)3 (5), [HC6N7(N[double bond, length as m-dash]PCl3)3]Cl (6) were obtained by the Kirsanov reaction of melamine (1–3) and melem (5 and 6) with halogenated phosphorus compounds. The products were characterized by FTIR and solution NMR spectroscopy as well as by single-crystal X-ray diffraction. Additionally, in order to investigate the electron density distribution in the s-triazine or s-heptazine systems combined with the phosphinimine group, and to understand the influence of protonation on the triazine and heptazine moieties, quantum chemical analyses of compounds 2, 3, 5 and 6 were performed. Furthermore, by reaction of 5 with phenol the compound C6N7(N[double bond, length as m-dash]P(OPh)3)3 (7) was obtained. Its potential application as a flame retardant was examined by the UL 94 flammability test.

Graphical abstract: Melem- and melamine-derived iminophosphoranes
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