Dynamische NMR-Untersuchungen Von Phosphorylierten Diamin-Gekoppelten Bis-1,3,5-Triazinen

Insight into the Synthesis and Characterization of Organophosphorus-Based Bridged Triazine Compounds

“…However, the 31 P-NMR spectrum of EDA-bis-TEPT showed two resonances assigned to an AB spin system, with a 31 P– 31 P coupling constant of about 8.8 Hz. Owing to the presence of the electron-donating NH groups next to the triazine ring, the two phosphorous atoms became inequivalent, and consequently, two different signals were observable at ambient temperatures [33]. The electron-donating ability of the NH group could influence the electron densities around the triazine carbons of EDA-bis-TEPT that bind directly to the phosphorus atoms, as confirmed by X-ray analysis (Table 1 and Figure 1).…”

“…It can be assumed that by replacing one phosphonate group with an electron-donating atom, such as nitrogen, the electron density of the triazine ring increases, thus decreasing the reactivity of the ring for further substitution reactions at ambient conditions [31]. On the contrary to the previous report [33], this methodology led to producing pure products that were isolated as solids. Hence, the correlation between the NMR spectroscopy and single crystal X-ray analysis provided an insight into the chemical structure of these products.…”

“…This synthetic process enabled the preparation of bridged triazine compounds in high yields and with a high purity as solids. The synthesis of the ethylene diamine-based bridged triazine compound is already reported in the literature, however, its detailed chemical and thermal characterizations are missing [33]. Bridged compounds, being larger structures, are expected to be thermally more stable.…”

Direct Phosphonylation of Aromatic Azaheterocycles

“…The phosphonylation of triazine-related heterocyclic ringsystems 263a − n (bis(4,6-dichloro-1,3,5-triazin-2-yl)diamines) was also achieved via an Arbuzov reaction . The procedure was analogous to the ones previously described, − using trialkyl phosphites and heating, but the substrates differed (Scheme and Table ).…”

An efficient microwave-assisted synthesis and biological properties of polysubstituted pyrimidinyl- and 1,3,5-triazinylphosphonic acids

“…5 Later it was shown that reactivity of various phosphorous esters in the MeA reaction decreases in the order of increasing electron-withdrawing effect of the substituents on the phosphorus atom. 6 Furthermore, a replacement of the chlorine atom in 4,6-disubstituted 2-chlorotriazines was studied, 7 and the MeA reaction was used to prepare a series of N,N 0 -bis [(dialkylphosphono)-1,3,5-triazin-2-yl]diamines in high to moderate yields.…”