Boron Lewis reagent with nitrogen and oxygen adducts: synthesis of aza-belted diazabicyclo[n.n.5.5]alkane derivatives

Abstract

A novel belt shape of multi-phenyl groups around a diazabicyclo[n.n.5.5]alkane center combined with boron, nitrogen, and oxygen adducts was prepared in good yield in two steps starting from phenylethylamine and 1,2-bis(chloromethyl)benzenes. The halogen boron adduct, XFY-3, 4, 5 and 6, showed unique nuclear magnetic resonance (NMR) spectroscopic properties. A series of 1H, 13C, 11B, and 19F NMR spectroscopy analysis revealed the change in chemical shifts were due to an interaction between the functional groups, and the XFY-6 was characteristic bands were analyzed by ultraviolet–visible absorption spectrum and fluorescence spectra. In particular, XFY-6 was an electron-rich compound because of its unique structure and excellent stability in terms of chemical reactivity.