Syntheses of (N → B)phenyl[N-alkylaminodiacetate-O,O′,N]boranes

Article abstract of DOI:10.1016/0277-5387(96)00109-X

The syntheses of (N → B)phenyl[N-alkylaminodiacetate-O,O′,N]boranes (2 to 6) and their corresponding N-alkylaminodiacetic acids (7 to 10) are reported. All compounds (except 6) were characterized by ¹H, ¹¹B (for boron heterocycles), ¹³C NMR, infrared spectroscopy and mass spectrometry. The ¹H NMR spectrum of compound 3 shows that it is a chiral molecule, its structure was determined by homonuclear decoupling experiments, ¹H NMR and HETCOR. The study of the intramolecular N → B coordination by dynamic NMR afforded a ΔG? value of 98.4 kJ mol^-1 for compound 3. Copyright