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Topic: Mechanism of CN-NH2 cyclization  (Read 3493 times)

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Offline Rutherford

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Mechanism of CN-NH2 cyclization
« on: October 25, 2013, 11:45:20 AM »
What is the mechanism of the attached reaction? What rearrangements are happening?
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Offline AlphaScent

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Re: Mechanism of CN-NH2 cyclization
« Reply #1 on: October 25, 2013, 02:27:58 PM »
This is an awesome question...  What is more likely to shift a cyano group or an amino group?  Seems like neither, but it has to happen..
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Offline orgopete

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Re: Mechanism of CN-NH2 cyclization
« Reply #2 on: October 25, 2013, 02:58:20 PM »
It looks like an elimination/addition of cyanide. I don't know if that is a homolytic or heterolytic reaction. The readdition adds the nitrogen to give a net isomerization. You should complete it from there.
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Offline Rutherford

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Re: Mechanism of CN-NH2 cyclization
« Reply #3 on: October 26, 2013, 03:54:13 AM »
I don't understand. There are two different nitrogens. Which one adds to what?
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Offline Archer

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Re: Mechanism of CN-NH2 cyclization
« Reply #4 on: October 26, 2013, 07:52:10 AM »
Is this just general interest or part of an assignment?

At least make an attempt at the problem.
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Offline orgopete

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Re: Mechanism of CN-NH2 cyclization
« Reply #5 on: October 26, 2013, 08:49:19 AM »
A heterolytic cleavage is easier to do. Start with the electrons on the nitrogen and form cyanide and a ketamine as the immonium form. Re-add cyanide using the nitrogen.
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Offline Rutherford

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Re: Mechanism of CN-NH2 cyclization
« Reply #6 on: October 26, 2013, 09:25:58 AM »
Then it may be something like this.
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