Synthesis and structural analysis of conjugated benzoxazaborine derivatives.

Graphical abstract Highlights • A novel boron-containing compound, benzoxazaborine, was synthesized. • The obtained benzoxazaborines were reasonably stable to hydrolysis. • The oxazaborine ring was the highly planar structure. • The B N bond length indicated an extended π-conjugated system. Abstract Benzoxazaborine derivatives were synthesized by the dehydration condensation reaction of 2-aminobenzyl alcohols with arylboronic acids. The insensitivity of the benzoxazaborines to hydrolysis allowed these compounds to be isolated by silica gel column chromatography. The single crystal X-ray structural analysis demonstrated the highly planar structure of the benzoxazaborine unit, and the B N bond length indicated an extended π-conjugated system. [ABSTRACT FROM AUTHOR]