Re: ORGLIST:Re: Hexa-aminobenzene

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From: Jacob Zabicky (zabicky$##$bgumail.bgu.ac.il)
Date: Tue Jul 23 2002 - 11:30:36 EDT


Hello Dave,

You can begin with 1-chloro-2,4-dinitrobenzene, quite a popular reagent for
the amino acid, polypeptide and protein set. The chloro will be easily
knocked out by ammonia. The same will happne with picryl chloride that is
not too bad to handle in small amounts. after partial or total reduction of
the nitro groups you are not too badly off target, hopefully.

All the best,

Jacob

At 15:34 23/7/2, David Kelly wrote:
>I wish to make hexa-aminobenzene. The same literature method has
>been used by all previous workers ie nucleophilic addition of ammonia
>or a synthetic equivalent (eg benzylamine) to 1,3,5-tri-nitrobenzene
>with in situ reoxidation, followed by reduction of the nitro groups.
>HOWEVER 1,3,5-tri-nitrobenzene is a military grade explosive and
>although it is reported to have low sensitivity to detonation, the safety
>committee, would go ballistic (literally..............).. Has anybody got any
>sharp ideas for a new synthesis. I would be prepared to tolerate no
>more than two nitro groups in an intermediate.
>
>Thanks
>
>Dave
>
>Dr David R. Kelly
>Dept. of Chemistry, Cardiff University, PO Box 912, Cardiff, CF10
>3TB, UK
>Phone 02920-874063: Fax 02920-874030
>Mobile 07971-240448: Home 02920-610891
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>http://www.semiochemica.org.uk/articles/articlesidx.html
>BEST Record: http://expertise.cos.com/cgi-bin/exp.cgi?id=498275
>For catalysis see http://www.chemsoc.org/cgi-
>shell/events/nforedisp.pl?ID=551
>Cardiff University is the public name of the University of Wales,
>Cardiff, a constituent institution of the
>University of Wales.
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Prof. Jacob Zabicky
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