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The synthesis of nine (N→B) phenyl substituted[N-benzyliminodiacetate-O,O’,N]boranes 3a-3i is reported herein. These compounds were characterized by H, C, B, HETCOR, NOESY, infrared spectroscopy, mass spectrometry and in the case of compounds 3d and 3g also by F NMR. All compounds exhibit a bicyclic structure due to the presence of an intramolecular N→B coordination bond. The structure of 4-chlorophenyl[N-benzyliminodiacetate-O,O’,N]borane 3e was further established by a single crystal x-ray diffraction study. The correlation between δ(B) of compounds 3a, 3d-3i and σHammett values shows that the strength of the N→B bond depends on the electronic factors of the substituent on the B-phenyl group.

Synthesis and characterization of new (N→B) phenyl substituted[N-benzyliminodiacetate-O,O′,N]boranes