Re: ORGLIST: A protocol for using N-chlorosuccinimmide

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From: Sorin Filip (sorin.filip$##$uni-bielefeld.de)
Date: Mon Feb 25 2002 - 11:41:38 EST

Hello Andrea !

I am currently doing chlorination of oximes using tert-butyl
hypochlorite, in water free dichloromethane, at -10 C. It's working very
well even for very sterically hindered oximes, e.g.
2,2,6,6-tetramethylcyclohexanone oxime, or sugars. For work-up, wash the
blue organic phase with sodium carbonate sat. sol., and then brine. Be
carefull when you prepare the tert-butyl hypochlorite solution; it
should be as concentrate as you can get it.
You can also take look at: Defoin, Albert; Joubert, Muriel; Heuchel,
Jean-Marc; Strehler, Christiane; Streith, Jacques; Synthesis; 12; 2000;
1719-1726.

Best reagards,
Sorin Filip

Andrea Giordano wrote:

> hello there! As previously reported (Organic Prep. and Proced. Int.,
> 19:329-426(1985)) chlorination over oximes may be carried out using
> NCS - N-chlorosuccinimmide - in order to obtain gem chloronitroso comp
> . I have never used such reagent, moreover the article in my hand
> doesn't give any specific reference. I looked up in Fieser's, but I
> didn't find any procedure involving NCS and oximes. Can anybody of you
> give me some hints about a possible protocol, please? Thanks very
> much! Andrea GiordanoCNR-IMCRome, Italy. 

--
Sorin Filip

Uni Bielefeld
Fakultaet fuer Chemie, OC III
Universitaetsstraße 25, Bielefeld
D-33615, Germany

Work: +49-(0)521-106 2144, 2147
Home: +49-(0)521-911 6310
email: sorin.filip$##$uni-bielefeld.de
http://oc3web.chemie.uni-bielefeld.de/english/org/wm2.html

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