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Halogenomercury Salts of Sterically Crowded Triazenides – Convenient Starting Materials for Redox‐Transmetallation Reactions
Author(s) -
Hauber SvenOliver,
Woo Seo Jang,
Niemeyer Mark
Publication year - 2010
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200900482
Subject(s) - transmetalation , chemistry , tetrahydrofuran , redox , steric effects , yield (engineering) , alkaline earth metal , inorganic chemistry , melting point , mass spectrometry , nuclear chemistry , medicinal chemistry , organic chemistry , alkali metal , catalysis , materials science , chromatography , solvent , metallurgy
Diaryl‐substituted triazenides Ar(Ar′)N 3 Hg X [Ar/Ar′ = Dmp/Mph, X = Cl ( 2a ), Br ( 3a ), I ( 4a ); Ar/Ar′ = Dmp/Tph, X = Cl ( 2b ), I ( 4b ) with Mph = 2‐MesC 6 H 4 , Mes = 2,4,6‐Me 3 C 6 H 2 , Tph = 2′,4′,6′‐triisopropylbiphenyl‐2‐yl and Dmp = 2,6‐Mes 2 C 6 H 3 ] were synthesized by salt‐metathesis reactions in ethyl ether from the readily available starting materials Ar(Ar′)N 3 Li and Hg X 2 . These compounds may be used for redox‐transmetallation reactions with rare‐earth or alkaline earth metals. Thus, reaction of 4b or 2b with magnesium or ytterbium in tetrahydrofuran afforded the triazenides Dmp(Tph)N 3 MX (thf) ( 5b : M = Mg, X = I; 6b : M = Yb, X = Cl) in good yield. All new compounds were characterized by melting point, 1 H and 13 C NMR spectroscopy and for selected species by IR spectroscopy or mass spectrometry. In addition, the solid‐state structures of triazenides 2a , 2b , 3a , 4b , 5b and 6b were investigated by single‐crystal X‐ray diffraction.