ORGLIST: Aryl sulfides

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From: Jon Kremsky (jkremsky$##$primeorg.com)
Date: Fri Feb 03 2006 - 18:20:04 EST

I have been trying to make a particular symmetrical diaryldisulfide from a
2-aminobenzoic acid with diazonium chemistry using an established literature
prep (Org Syn, CV2, p 540) with disodium disulfide as the reagent. I
invariably get the aryl thiol rather than the disulfide that everyone else
seems to obtain. I can dimerize with air, but I do not understand the
problem. Any suggestions?

Also, as a way around the problem, is there a good method to substitute an
aryl bromide for sulfur directly? for example, 2-bromobenzoic acid to
thiosalicylic acid?

Any help is appreciated.

Jonathan N. Kremsky


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