Re: ORGLIST: Bamberger rearrangement

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From: srinivas reddy (gounisrinivas$##$yahoo.com)
Date: Mon Sep 25 2006 - 02:53:09 EDT

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In reply to: antonio regla: "ORGLIST: Bamberger rearrangement"

Hi,
The Bamberger rearrangement is the chemical reaction
of N-phenylhydroxylamines with strong aqueous acid,
which will rearrange to give 4-aminophenols.
N-Phenylhydroxylamines are typically synthesized from
nitrobenzenes by reduction using rhodium or zinc.

The mechanism of the Bamberger rearrangement proceeds
from the monoprotonation of N-phenylhydroxylamine.
N-protonation is favored, but unproductive.
O-protonation can form the nitrenium ion , which can
react with nucleophiles (H2O) to form the desired
4-aminophenol.

here is some procedure from organic syntheses. please
follow the link.

http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0148

good luck
cheers

--- antonio regla <areglac$##$yahoo.com> wrote:

> Dear List members:
> I am looking for references on the synthetic aspects
> of the Bamberger rearrangement. So far I've only
> found references on mechanistic aspects of this
> reaction, and no details on how to carry out this
> reaction in the lab, that is conditions, reagents,
> temperatures, etc. I would appreciate any help you
> may give me.
> Sincerely.
> Dr. Antonio Regla>
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Next message: ze han: "ORGLIST: dechlorination of aromatic chrorides"
Previous message: sohayb mohammed: "ORGLIST: oxidation by DDQ"
In reply to: antonio regla: "ORGLIST: Bamberger rearrangement"

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