Influence of the silyl group on the reactivity of some ortho-lithiated aryl alkyl sulfides

Krzysztof Durka , Tomasz Kliś , Janusz Serwatowski , Krzysztof Woźniak

Abstract

The 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.
Author Krzysztof Durka (FC / DPC)
Krzysztof Durka,,
- Department Of Physical Chemistry
, Tomasz Kliś (FC / DPC)
Tomasz Kliś,,
- Department Of Physical Chemistry
, Janusz Serwatowski (FC / DPC)
Janusz Serwatowski,,
- Department Of Physical Chemistry
, Krzysztof Woźniak - [University of Warsaw (UW)]
Krzysztof Woźniak,,
-
- Uniwersytet Warszawski
Journal seriesOrganometallics, ISSN 0276-7333
Issue year2013
Vol32
No11
Pages3145-3148
Publication size in sheets0.5
ASJC Classification1604 Inorganic Chemistry; 1605 Organic Chemistry; 1606 Physical and Theoretical Chemistry
DOIDOI:10.1021/om400236x
URL http://pubs.acs.org/doi/abs/10.1021/om400236x
Languageen angielski
File
organometallics_2013_32_3145.pdf 601.2 KB
Score (nominal)40
Score sourcejournalList
ScoreMinisterial score = 40.0, 02-02-2020, ArticleFromJournal
Ministerial score (2013-2016) = 40.0, 02-02-2020, ArticleFromJournal
Publication indicators Scopus Citations = 2; WoS Citations = 2; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 0.983; WoS Impact Factor: 2013 = 4.253 (2) - 2013=3.817 (5)
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