Über die Umsetzung von Phosphorverbindungen mit dem Strukturelement P(:X)H (X = O, S) mit 1,3,5-Trimethylhexahydro-1,3,5-triazin. Darstellung und Reaktionen α-(N-Methylamino)methyl-substituierter Phosphorverbindungen / Reactions of Phosphorus Compounds Containing the P(:X)H Group (X = O, S) with 1,3,5-Trimethylhexahydro-1,3,5-triazine. Synthesis and Reactions of α-(N-Methylamino)methyl Substituted Phosphorus Compounds

Abstract

The reactions of the acids la-4a and 8a with 1,3,5-trimethylhexahydro-1,3,5-triazine furnished compounds 1b-4b and 8b. The IR investigation of 1 b, 4b and 8b revealed P=O ··· H—N interactions. In the unusual reaction of lb with methyl iodide the quaternary ammonium iodide [(H3C)2P(:O)CH2N(CH3)3]+I- 1c was formed. The reaction of 2b with methyl iodide produced the ammonium iodide [(H3C)2P(:S)CH2NH2CH3]+I- 2c. The structure of 2c was confirmed by X-ray crystal structure analysis, which showed the expected distorted tetrahedral geometry at phosphorus and revealed N—H ••• I hydrogen bonds. Reaction of 8b with methyl iodide led to the formation of the ammonium iodide 8c by methylation at the nitrogen atom. In the reaction of lb and 2b with HPF6 the compounds 1 d and 2d were obtained. The compounds 1 d and 2d, due to their instability at room temperature, could be identified only by 1H and 31P NMR spectroscopy.