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Topic: Aryl acetilene  (Read 6782 times)

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Offline alexanderdundua

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Aryl acetilene
« on: June 21, 2008, 11:49:52 AM »
Hello everyone?
I have a question.
Is the following reaction possible or not.

Offline spirochete

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Re: Aryl acetilene
« Reply #1 on: June 21, 2008, 02:09:49 PM »
What kind of potential reaction (or reactions) are we considering here as possibilities?

What are the requirements for these potential reactions?

Offline macman104

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Re: Aryl acetilene
« Reply #2 on: June 21, 2008, 02:57:41 PM »
I'm assuming some sort of nucleophilic aromatic substitution?

Offline spirochete

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Re: Aryl acetilene
« Reply #3 on: June 21, 2008, 02:58:29 PM »
yup I thought maybe he'd figure that out  :P

Offline macman104

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Re: Aryl acetilene
« Reply #4 on: June 21, 2008, 03:36:06 PM »
yup I thought maybe he'd figure that out  :P
Oh, my bad.  I viewed him asking, a hypothetical, will this type of reaction go.  As in possibly understanding what was going on, but not sure if this specific variation will happen...

EDIT:  In hindsight, I completely glossed over your hint and viewed it as a clarification question.  It reads completely like a hint now.

Offline superg

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Re: Aryl acetilene
« Reply #5 on: June 22, 2008, 07:00:45 AM »
hello,
the preparation of this compound by this way could be very hard, the sodium compound should be very unstable...
if you want ot prepare this type of compound, the best way is the sonogashira coupling, between the alkyne and the aryl bromide (or iodide) with palladium catalyst and cupper I salt (in fact it's the Cu-C(tplebond)C who react with the paladium catalyst)
have a look to that : http://www.organic-chemistry.org/namedreactions/sonogashira-coupling.shtm
bye

Offline alexanderdundua

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Re: Aryl acetilene
« Reply #6 on: June 22, 2008, 07:30:59 AM »
hello,
the preparation of this compound by this way could be very hard, the sodium compound should be very unstable...
if you want ot prepare this type of compound, the best way is the  sonogashira coupling, between the alkyne and the aryl bromide (or iodide) with palladium catalyst and cupper I salt (in fact it's the Cu-C(tplebond)C who react with the paladium catalyst)
have a look to that : http://www.organic-chemistry.org/namedreactions/sonogashira-coupling.shtm
bye

Tanks for suggestion!
But the problem is that I have not and can't get the catalyst required for sonogashira-coupling.
I know that sodium acetylide is very unstable and explosive, but I can deal with that. Thing that worries me is that I'm not sure if this reaction proceeds with formation of desired product. R-C6H4-C(tplebond)CH

Offline HP

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Re: Aryl acetilene
« Reply #7 on: June 23, 2008, 02:56:40 PM »
Also possible reaction of your aryl bromid with Iotsich reagent - alkyne-Grignard:

R-C6H5-Br + C2H2-MgBr = R-C6H5-C2H
xpp

Offline kiwi

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Re: Aryl acetilene
« Reply #8 on: June 23, 2008, 09:18:30 PM »
Quote
Tanks for suggestion!
But the problem is that I have not and can't get the catalyst required for sonogashira-coupling.
I know that sodium acetylide is very unstable and explosive, but I can deal with that. Thing that worries me is that I'm not sure if this reaction proceeds with formation of desired product. R-C6H4-C(tplebond)CH

I doubt it will go, and the sodium acetylide is the least of your probelms. Disconnecting the other side of the acetylene  (to give an aryl acetylene anion + alkyl halide in the forward sense) is a better idea.

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