1,2-Azaborine: The Boron-Nitrogen Derivative of ortho-Benzyne

Angew Chem Int Ed Engl. 2015 Jun 26;54(27):7819-22. doi: 10.1002/anie.201502967. Epub 2015 Jun 11.

Abstract

The BN analogue of ortho-benzyne, 1,2-azaborine, is generated by flash vacuum pyrolysis, trapped under cryogenic conditions, and studied by direct spectroscopic techniques. The parent BN aryne spontaneously binds N2 and CO2, thus demonstrating its highly reactive nature. The interaction with N2 is photochemically reversible. The CO2 adduct of 1,2-azaborine is a cyclic carbamate which undergoes photocleavage, thus resulting in overall CO2 splitting.

Keywords: ab initio calculations; arynes; boron; matrix isolation; nitrogen heterocycles.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemistry*
  • Boron / chemistry*
  • Boron Compounds / chemistry*
  • Carbamates / chemistry
  • Carbon Dioxide / chemistry
  • Models, Molecular
  • Nitrogen / chemistry*

Substances

  • 1,2-azaborine
  • Benzene Derivatives
  • Boron Compounds
  • Carbamates
  • benzyne
  • Carbon Dioxide
  • Nitrogen
  • Boron