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Neuartige Silane mit sterisch anspruchsvollen Aryl‐Substituenten
Author(s) -
Weidemann Nils,
Schnakenburg Gregor,
Filippou Alexander C.
Publication year - 2009
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.200800420
Subject(s) - silanes , steric effects , aryl , substituent , chemistry , silane , medicinal chemistry , transmetalation , silylation , crystal structure , stereochemistry , catalysis , crystallography , organic chemistry , alkyl
Novel Silanes with Sterically Demanding Aryl Substituents A series of novel m ‐terphenylsilanes was synthesized and fully characterized. Halogenation of Si(C 6 H 3 ‐2,6‐Trip 2 )H 3 ( 1 , Trip = C 6 H 2 ‐2,4,6‐ i Pr 3 ) with ICl and BI 3 afforded the m ‐terphenylmonochlorosilane Si(C 6 H 3 ‐2,6‐Trip 2 )H 2 Cl ( 2 ) and the m ‐terphenyldiiodosilane Si(C 6 H 3 ‐2,6‐Trip 2 )HI 2 ( 3 ), respectively. The chiral phosphanylmethylsilane Si(C 6 H 3 ‐2,6‐Trip 2 )HCl(CH 2 PMe 2 ) ( 6 ) was obtained by metathetical exchange of Si(C 6 H 3 ‐2,6‐Trip 2 )HCl 2 ( 4 ) with the Grignard reagent Me 2 PCH 2 MgCl ( 5 ). Similarly, metathetical exchange of SiBr 4 with 0.5 equiv. of {Li(C 6 H 3 ‐2,6‐Mes)} 2 ( 7 ) yielded the m ‐terphenyltribromsilane Si(C 6 H 3 ‐2,6‐Mes 2 )Br 3 ( 8 ). A Pd(II) catalyzed reaction of MesSiH 3 ( 10 ) with 2‐iodopropane afforded the triiodosilane MesSiI 3 ( 11 ) bearing the sterically less demanding mesityl substituent. The silanes were fully characterized and the molecular structures of compounds 2 and 11 were determined by single‐crystal X‐ray diffraction.