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Topic: Dienone-phenol rearrangement  (Read 9560 times)

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Offline squeak

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Dienone-phenol rearrangement
« on: October 02, 2007, 01:48:24 PM »
Greetings.  :)

I'd appreciate if someone could confirm if the following mechanism of dienone-phenol rearrangement is correct.

Thanks.

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Offline agrobert

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Re: Dienone-phenol rearrangement
« Reply #1 on: October 02, 2007, 05:44:37 PM »
Mechanism is reasonable and the formation of a five membered ring attached to a aromatic substituted benzene seems favorable.
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In the realm of scientific observation, luck is only granted to those who are prepared. -Louis Pasteur

Offline D|0XIN

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Re: Dienone-phenol rearrangement
« Reply #2 on: October 04, 2007, 05:26:02 AM »
Hi :D

I agree that it looks reasonable - all the arrow pushing is perfect.

This rearrangement looks thermodynamically favourable due to expansion of the highly strained spiro cyclobutane ring which would lessen upon expansion.
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Offline AWK

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Re: Dienone-phenol rearrangement
« Reply #3 on: October 04, 2007, 06:01:26 AM »
At the third step (fouth picture) H+ should leave molecule, not rearrange.
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AWK

Offline squeak

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Re: Dienone-phenol rearrangement
« Reply #4 on: October 05, 2007, 01:43:07 AM »
Indeed, AWK. It's only that that arrow is a little big in the fourth structure so it might look as if H rearranges.  :)
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