Re: ORGLIST: sulfide to sulphone

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From: Jacob Zabicky (zabicky$##$bgumail.bgu.ac.il)
Date: Tue Mar 05 2002 - 11:13:29 EST

Hello Witek,

Hopefully these old recipes for sulphone synthesis will be useful. IMHO, if
your sulfides are too volatile you'll find the ozone method quite difficult
to apply.

R. Pumerer, Ber, 43, 1407 (1910) prepared diethyl sulphone with hydrogen
peroxide (very slow synthesis).

O. Hisberg, Ber. 43, 289 (1910) prepared diphenyl sulphone whith the same
reagent.

R. W. Boost et al. JACS 54 1986 (1932) used permanganate in glacial acetic
acid to oxidize 2,4-dinitrophenyl thioethers to the sulphones. See also R.
Otto, Ber. 13, 1272 (1880), E. Beckmann, J. pr. Chem., (ii) 17, 441 (1878).

All the best,

Jacob

At 11:02 04/03/2002, Witek Mozga wrote:
>Hello everybody,
>
>I want to oxidize thioether (R-S-R) to obtain sulfone (R-SO2-R). I
>heard that Oxone should work in this case. Can anybody give me a
>typical procedure for using Oxone?
>
>Thanks in advance
>
>Witek Mozga
>TriMen Chemicals
>http://www.trimen.pl/

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Prof. Jacob Zabicky
Institutes for Applied Research
Ben-Gurion University of the Negev Private: POB 12366, Beer-Sheva 84863
POB 653, Beer-Sheva 84105, ISRAEL Tel. +972-8-6496792
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