Re: ORGLIST - orglist Digest - V01 #39

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From: by way of Joao Aires de Sousa (sukenc$##$gefen.cc.biu.ac.il)
Date: Sun Jun 15 1997 - 03:20:34 EDT


On Fri, 13 Jun 1997 orglist-request$##$dq.fct.unl.pt wrote:
>
> Date: Thu, 12 Jun 1997 15:06:29 -0400
> From: "Timothy L. Friebe" <tlf5$##$psu.edu>
> Subject: Cl3SiLi
> I am currently in need of a method for synthesizing primary alkyl
> trichlorosilanes preferably without adding H-SiCl3 across a double bond.
> Is it possible to generate Li-SiCl3 (from H-SiCl3 and n-BuLi) and then do
> an SN2 reaction on a primary alkyl tosylate? The alkyl group desired
> already has an internal double bond which would cause problems when doing a
> hydrosilation. Any help would be appreciated! Thanks in advance.
> Tim Friebe

The more common solution to this problem is to use an alkyl Grignard and
react it with SiCl4. This reaction is not the best behaved in the world so
good alternatives (either as you suggest or in the form of procedures
using other organometallics) would still be useful.
Good luck,
/Chaim Sukenik

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