RE: ORGLIST:oxidation of pyrrole under acidic condition

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From: Boyles, David A. (David.Boyles$##$
Date: Thu Jul 25 2002 - 11:46:53 EDT


The pine splint test for pyrrole has been long noted.
A pine splint dipped in HCl will turn red when introduced into a test tube
containing pyrrole.
The mechanism is simply an acid-promoted polymerization, pyrrole being pi
excessive. Further oxidation in the presence of oxygen may occur to afford
a more intensely-colored, conjugated polymer.
David A. Boyles
Professor of Chemistry
Department of Chemistry and Chemical Engineering
South Dakota School of Mines and Technology
Rapid City, SD 57701

-----Original Message-----
From: Yantao Chen [mailto:yantao$##$]
Sent: Thursday, July 25, 2002 6:18 AM
To: 'everybody$##$'
Subject: ORGLIST:oxidation of pyrrole under acidic condition

Dear All:
Recently I once try the oxidation of pyrrole with organic or inorganic acid
at the presence of oxidants. However, much interestingly, when heated,
pyrrole can be polymerized even without any oxidants under acidic water
solutions, such like HCl and H2SO4? The concentration of these two acids
solutions are about 0.1 M. My first question is that if the polymerization
took place., and the second one is about the mechanism. Can anyone help me

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