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Dienone-phenol rearrangement
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Topic: Dienone-phenol rearrangement (Read 9737 times)
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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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agrobert
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diels alder
Re: Dienone-phenol rearrangement
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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
D|0XIN
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Re: Dienone-phenol rearrangement
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Reply #2 on:
October 04, 2007, 05:26:02 AM »
Hi
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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AWK
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Re: Dienone-phenol rearrangement
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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
squeak
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Re: Dienone-phenol rearrangement
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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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Dienone-phenol rearrangement