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Topic: regioselectivity question  (Read 1815 times)

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Offline mana

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regioselectivity question
« on: June 04, 2018, 03:42:01 AM »
Hi
In this reaction which product is dominant? I know steric effect should be considered, but both of them, I think has hindered substituents

Offline sjb

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Re: regioselectivity question
« Reply #1 on: June 04, 2018, 04:11:18 AM »
Perhaps also consider electronics?

Offline rolnor

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Re: regioselectivity question
« Reply #2 on: June 04, 2018, 05:31:27 AM »
I have lithiated fluoroaromatics and you can also get attack from one of the lithiated aromatics on the benzyne to get a biphenyl. I think the product in your scheme with the charge ortho to the methoxygroup is more stable.

Offline crawlingmcedge

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Re: regioselectivity question
« Reply #3 on: June 07, 2018, 02:54:31 PM »
Draw out the resonance structures for both products.

Consider the electronic nature of the OMe group? EWG? EDG? Which one would be the most stable?

Offline mana

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Re: regioselectivity question
« Reply #4 on: June 10, 2018, 04:18:24 AM »
Draw out the resonance structures for both products.

Consider the electronic nature of the OMe group? EWG? EDG? Which one would be the most stable?
Both seem terrible: -\ isn't it?
but the second is like a betaien

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