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Topic: Diazonium question  (Read 2764 times)

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Offline zsinger

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Diazonium question
« on: July 26, 2014, 01:59:41 PM »
All,
Why is F- particularly hard to attach to the aryl diazonium chloride ring without BF4 and an acidic workup step?  I- same thing?
         -Zack
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Offline discodermolide

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Re: Diazonium question
« Reply #1 on: July 26, 2014, 02:03:43 PM »
This is the Schiemann reaction. I don't think the mechanism is really well known.
http://www.organic-chemistry.org/namedreactions/balz-schiemann-reaction.shtm

Take from this what you will.

But it does work and quite well.
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Offline zsinger

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Re: Diazonium question
« Reply #2 on: July 27, 2014, 09:25:46 AM »
Perhaps BF4- acts as a " delivery agent".
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Offline discodermolide

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Re: Diazonium question
« Reply #3 on: July 27, 2014, 11:25:01 AM »
Could be. The proposed mechanism on the wiki page seems a bit strange.
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Offline zsinger

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Re: Diazonium question
« Reply #4 on: July 27, 2014, 02:55:49 PM »
(Or lack thereof) :)
      -Z
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