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Efficient Synthesis of a NHC‐Coordinated Trisilacyclopropylidene and Its Coordination Behavior
Author(s) -
Guddorf Benedikt J.,
Hepp Alexander,
Lips Felicitas
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802625
Subject(s) - diphenylacetylene , carbene , chemistry , ring (chemistry) , yield (engineering) , medicinal chemistry , adduct , double bond , stereochemistry , silylene , catalysis , organic chemistry , materials science , metallurgy , silicon
With a co‐reduction procedure using 2 equivalents Mes 2 SiCl 2 and 1 equivalent NHC i Pr2Me2 →SiCl 4 an NHC‐adduct of a trisilacyclopropylidene (SiMes 2 ) 2 SiNHC i Pr2Me2 1 was synthesized. Addition of NHC Me4 to 1 results in quantitative carbene exchange under release of NHC i Pr2Me2 to yield (SiMes 2 ) 2 SiNHC Me4 2 . Both NHC‐coordinated trisilacyclopropylidenes coordinate to BH 3 . In reaction of 1 with SiMe 3 N 3 a NHC‐coordinated trisilane with an exocyclic Si=N double bond is formed. With diphenylacetylene 1 undergoes a ring expansion at room temperature to afford a five‐membered ring compound with an NHC‐coordinated silylene functionality.