Clicking the Arsenic-Carbon Triple Bond: An Entry into a New Class of Arsenic Heterocycles

Gregor Pfeifer, Martin Papke, Daniel Frost, Julian A. W. Sklorz, Marija Habicht, Christian Müller – 2016

Arsaalkynes can undergo regioselective and quantitative [3+2] cycloaddition reactions with organic azides to give hitherto unknown 3H-1,2,3,4-triazaarsole derivatives. The reaction product was obtained as a white, air- and moisture-stable solid, and the presence of a planar, five-membered arsenic heterocycle was unambiguously verified by means of X-ray crystallography. DFT calculations gave insight into the electronic structure of these novel compounds compared to tetrazoles and triazaphospholes. The coordination chemistry towards Re(I) was investigated and compared with the structurally related phosphorus-containing ligand. These preliminary investigations pave the way for a new class of arsenic heterocycles and fill the gap between the azaarsoles already known.

Titel
Clicking the Arsenic-Carbon Triple Bond: An Entry into a New Class of Arsenic Heterocycles
Verfasser
Gregor Pfeifer, Martin Papke, Daniel Frost, Julian A. W. Sklorz, Marija Habicht, Christian Müller
Schlagwörter
Click-Chemistry
Datum
2016
Kennung
10.1002/anie.201605143
Erschienen in
Angew. Chem. Int. Ed. 2016, 55, 11760-11764.
Art
Text