Unpredictable reaction of phenyltrichlorosilane with tert-butyllithium

The reaction of PhSiCl3 with one equivalent of Li[tBu] at r. t. yielded tBuPhSiCl2 whereas tBu2PhSiCl was only a minor product of the reaction of two molar equivalents Li[tBu] with PhSiCl3 at 60°C. By contrast, at r. t. tBuPhSiCl2 was solely formed by this reaction. Treatment of PhSiCl3 with three o...

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Bibliographic Details
Published in:Inorganic chemistry communications 2014-06, Vol.44, p.50-52
Main Authors: Scholz, Stefan, Sänger, Inge, Schödel, Frauke, Bolte, Michael, Lerner, Hans-Wolfram
Format: Article
Language:English
Subjects:
Silanes
Silenes
tert-Butyllithium
X-ray structure analysis
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Summary:The reaction of PhSiCl3 with one equivalent of Li[tBu] at r. t. yielded tBuPhSiCl2 whereas tBu2PhSiCl was only a minor product of the reaction of two molar equivalents Li[tBu] with PhSiCl3 at 60°C. By contrast, at r. t. tBuPhSiCl2 was solely formed by this reaction. Treatment of PhSiCl3 with three or more equivalents of Li[tBu] at 98°C yielded a mixture of tBu2PhSiH and tBu2(tBuC6H4CMe2CH2)SiH (3). Both silanes could easily be separated from each other: tBu2PhSiH was distilled from the reaction mixture and the silane 3 could be crystallized from the dissolved distillation residue. X-ray quality crystals of 3 were grown from a benzene solution at ambient temperature (monoclinic, P21/c). [Display omitted] •Treatment of PhSiCl3 with 4eq. of Li[tBu] yields tBu2(tBuC6H4CMe2CH2)SiH at 98°C.•At r. t. tBuPhSiCl2 was solely formed by this reaction.•tBu2(tBuC6H4CMe2CH2)SiH crystallizes in the monoclinic space group P21/c.
ISSN:1387-7003
1879-0259
DOI:10.1016/j.inoche.2014.02.039