Influence of the silyl group on the reactivity of some ortho-lithiated aryl alkyl sulfides
Krzysztof Durka , Tomasz Kliś , Janusz Serwatowski , Krzysztof Woźniak
AbstractThe lithiation of brominated aryl (α-dimethylsilyl)alkyl sulfides in diethyl ether produces stable heterocyclic silanes, which were characterized by 1H, 13C, and 29Si NMR spectroscopy and by X-ray crystallography. The reaction involves the intramolecular attack of the phenyl carbanion on the silicon atom with the formation of a pentacoordinated silicon intermediate. The stability of the formed intermediate depends on the solvent. It decomposes easily in THF at -78 °C with Si-C bond cleavage; however, it is stable in diethyl ether at room temperature. Addition of water results in the Si–H bond cleavage, while the heterocyclic ring containing the silicon atom is conserved.
|Journal series||Organometallics, ISSN 0276-7333|
|Publication size in sheets||0.5|
|ASJC Classification||; ;|
|Score|| = 40.0, 02-02-2020, ArticleFromJournal|
= 40.0, 02-02-2020, ArticleFromJournal
|Publication indicators||= 2; = 2; : 2013 = 0.983; : 2013 = 4.253 (2) - 2013=3.817 (5)|
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