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Topic: Methoxy-methylene-cyclohexane under acidic condition?  (Read 4846 times)

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Offline kanonsviel

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Methoxy-methylene-cyclohexane under acidic condition?
« on: October 11, 2010, 02:14:58 AM »
I kinda remember that it would undergo a migration just like that of the oxime...but I'm not sure about the mechanism after the migration, would you please give me some hints?
Would it form a cycloheptanone? If that's correct then, which side did the water attack occur? ???

Offline ooosh

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Re: Methoxy-methylene-cyclohexane under acidic condition?
« Reply #1 on: October 11, 2010, 04:35:08 AM »
I think it will be a hydrolysis of the enol ether.

the H+ adds to the C which is far away from the OCH3 group,so the C cation formed will be stablized by the O atom ,which also has a more stable resonance the O bears a positive charge.
cycloheptanone may be a byproduct.

Offline discodermolide

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Re: Methoxy-methylene-cyclohexane under acidic condition?
« Reply #2 on: October 11, 2010, 05:53:14 AM »
I kinda remember that it would undergo a migration just like that of the oxime...but I'm not sure about the mechanism after the migration, would you please give me some hints?
Would it form a cycloheptanone? If that's correct then, which side did the water attack occur? ???


You will get cyclohexanone back.
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Offline Doc Oc

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Re: Methoxy-methylene-cyclohexane under acidic condition?
« Reply #3 on: October 11, 2010, 08:42:48 AM »
Actually, you get cyclohexanecarboxaldehyde.

http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=108464|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC

Offline discodermolide

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Re: Methoxy-methylene-cyclohexane under acidic condition?
« Reply #4 on: October 11, 2010, 10:44:17 AM »
Actually, you get cyclohexanecarboxaldehyde.

http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=108464|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC

sorry I can't count
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Offline kanonsviel

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Re: Methoxy-methylene-cyclohexane under acidic condition?
« Reply #5 on: October 12, 2010, 09:18:01 AM »
Quote
You will get cyclohexanone back.

would you please give me some details in mechanism?

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