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Clicking the Arsenic–Carbon Triple Bond: An Entry into a New Class of Arsenic Heterocycles
Author(s) -
Pfeifer Gregor,
Papke Martin,
Frost Daniel,
Sklorz Julian A. W.,
Habicht Marija,
Müller Christian
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201605143
Subject(s) - arsenic , cycloaddition , chemistry , regioselectivity , ligand (biochemistry) , triple bond , combinatorial chemistry , double bond , organic chemistry , biochemistry , receptor , catalysis
Arsaalkynes can undergo regioselective and quantitative [3+2] cycloaddition reactions with organic azides to give hitherto unknown 3 H ‐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.