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Topic: azirine reaction with CHCl3 / OH-  (Read 6575 times)

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Offline swati

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azirine reaction with CHCl3 / OH-
« on: October 02, 2007, 07:28:08 AM »
What is/are the expected product(s) in the following reaction and give mechanism

What I think is
1.)  CHCl3 will react with OH- to give carbene :CCl2
2.)  carbene will give addition reaction over N=C and gets attached over N

Pls tell me whether I am correct or not and what will happen after this (if I am correct)
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Offline agrobert

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Re: azirine reaction with CHCl3 / OH-
« Reply #1 on: October 02, 2007, 09:51:07 PM »
What is your source of hydroxide ion? Is it organic soluble? I believe chloroform is the solvent in this reaction and in that case you will open the azirine ring by hydrolysis with hydroxide.  Either the 1 or 2 position will be attacked depending on electronegativity and steric hindrance.  Think about it.
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Offline squeak

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Re: azirine reaction with CHCl3 / OH-
« Reply #2 on: October 03, 2007, 02:40:54 AM »
CHCl3 with OH- almost certainly generates dichlorocarbene in situ.

Swati, what are your 'A' and 'B'?

Are you doing a ring expansion after dichlorocarbene bonds to azirine? 
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Offline swati

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Re: azirine reaction with CHCl3 / OH-
« Reply #3 on: October 03, 2007, 02:47:35 AM »
I dont know what are A and B
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