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Topic: A question related to Hofmann elimination  (Read 1798 times)

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Offline ino

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A question related to Hofmann elimination
« on: March 05, 2014, 04:49:27 AM »
Please help me with this problem!
What is the mechanism of this reaction in the attached figure?
I think it is a reaction which starts with the Hofmann elimination, but I don't understand what happens after the elimination.

Offline clarkstill

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Re: A question related to Hofmann elimination
« Reply #1 on: March 05, 2014, 05:47:55 AM »
I don't think you can get there via a Hofmann pathway...

My guess is some sort of sigmatropic rearrangement followed by rearomatization; I've drawn a plausible mechanism from the methyl anion, but you could also get there from the benzylic anion.

Offline ino

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Re: A question related to Hofmann elimination
« Reply #2 on: March 05, 2014, 06:20:44 AM »
Thank you for answering!
So I am wrong at the very beginning...
May I ask why it won't just go through the Hofmann elimination pathway and yield an alkene product?

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