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Topic: Elimination-Addition: Benzyne  (Read 2188 times)

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Offline davidenarb

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Elimination-Addition: Benzyne
« on: August 04, 2014, 07:05:16 PM »
Hi all,

Bellow, we have an Elimination-Addition reaction.

Will we have two products if the conditions were : 1) NaOH, 350°C 2) H3O+ ? or it works only if the base is NaNH2 ?
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Offline rwiew

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Re: Elimination-Addition: Benzyne
« Reply #1 on: August 04, 2014, 08:03:58 PM »
NaOH won't be strong enough a base to form the benzyne. You could get an SNAr mechanism with a nucleophile like OH-, but you don't have an electron withdrawing group on the ring to facilitate that.
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Offline zsinger

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Re: Elimination-Addition: Benzyne
« Reply #2 on: August 04, 2014, 09:02:27 PM »
Amide usually works better, and the above is correct.  One needs a strong deactivator like nitro groups to facilitate SnAr.
          -Z
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Offline orgopete

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Re: Elimination-Addition: Benzyne
« Reply #3 on: August 05, 2014, 01:07:43 AM »
Quote from: davidenarb on August 04, 2014, 07:05:16 PM
Will we have two products if the conditions were : 1) NaOH, 350°C 2) H3O+ ? or it works only if the base is NaNH2 ?

Is this a literature procedure? If it is, then I think you will get a mixture.
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