Re: ORGLIST:tBuOCl in THF

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From: Yuehui Zhou (yuehuizhou$##$hotmail.com)
Date: Sat Jun 15 2002 - 05:00:49 EDT


You may use ionic liquids as solvent. Ionic liquids are quite in trend to
replace traditional solvents. They have high solubilizing ability for many
compounds, don't evaporate and can be heated to as high as 200 C. You can
evaporated your product under high vacuum from the ionic liquid and reuse
it. There are many published papers on Friedel Crafts reactions in ionic
liquids. Most author believe that ionic liquids facilitate the reactions.
One paper even mentioned the reaction without Luis acid as catalyst.

I am working with phosphonium ionic liquids for quite a while. Phosphonium
chloride could be your choice as solvent.

Yuehui Zhou

>From: Andrea Giordano <andrea.giordano$##$mlib.cnr.it>
>To: everybody$##$orglist.net
>Subject: ORGLIST:tBuOCl in THF
>Date: Wed, 12 Jun 2002 23:09:24 +0200
>
>Hello all!
>
>In the past I experienced how THF is unsuitable for chlorination by means
>of
>gaseous Cl2, as THF chlorinates itself.
>
>On the one hand, I moved to tertbutyl hypochlorite (tBuOCl), which is
>particulary suited for my substrates;on the other hand, one I intend to
>chlorinate particulary "likes" THF, i.e. is insoluble in methylen chloride
>or chloroform, (other than common solvents) where it sticks on the wall of
>the reaction vessel decreasing significantly my desired yield...
>
>I decided to try tBuOCl/THF, but I don't know in principle if the solvent
>can stand it...At a first sight, it seems I don't have a messy TLC as
>happend with THF/CL2, anyway what do you think about it?
>
>Thanks!
>
>A. Giordano
>CNR-IMC
>Rome, Italy.
>
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