REACTIONS OF PHOSPHORUS-COMPOUNDS CONTAIN ING THE P(-X)H GROUP (X=O, S) WITH 1,3,5-TRIMETHYLHEXAHYDRO-1,3,5-TRIAZINE - SYNTHESIS AND REACTIONS OF ALPHA-(N-METHYLAMINO)METHYL SUBSTITUTED PHOSPHORUS-COMPOUNDS

The reactions of the acids 1a-4a and 8a with 1,3,5-trimethylhexahydro- 1,3,5-triazine furnished compounds 1b-4b and 8b. The IR investigation of 1b, 4b and 8b revealed P=O...H-N interactions. In the unusual react ion of 1b 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 structu re of 2c was confirmed by X-ray crystal structure analysis, which show ed the expected distorted tetrahedral geometry at phosphorus and revea led N-H...I hydrogen bonds. Reaction of 8b with methyl iodide led to t he formation of the ammonium iodide 8c by methylation at the nitrogen atom. In the reaction of 1b and 2b with HPF6 the compounds 1d and 2d w ere obtained. The compounds 1d and 2d, due to their instability at roo m temperature, could be identified only by H-1 and P-31 NMR spectrosco py.