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A vial of pyrrole (that was occasionally exposed to air) changed its color while degrading from pale yellow to dark orange.

What is the mechanism of pyrrole degradation? What are the resulting products?

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    $\begingroup$ Off the top of my head, I'd guess that you'd get some oxidation, some dimerization or polymerization, and some portion of Lewis-acid-base complex on the nitrogens. Most papers I've read about pyrrole polymerization will protect the N-H before doing chemistry. $\endgroup$ – Geoff Hutchison Aug 4 '15 at 21:52
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    $\begingroup$ Hopefully, not pyrolysis. ;-) $\endgroup$ – DrMoishe Pippik Aug 4 '15 at 22:33
  • $\begingroup$ Is there acid present? $\endgroup$ – Jori Aug 5 '15 at 8:25
  • $\begingroup$ @Jori, no, not really $\endgroup$ – Sparkler Aug 5 '15 at 13:19
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    $\begingroup$ @Sparkler It is probably polymerization of the oxidized pyrrole then. I figure that the mechanism for the polymerization is the same as for the (Lewis) acid initialized mechanism. $\endgroup$ – Jori Aug 5 '15 at 13:57

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