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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: ino on March 05, 2014, 04:49:27 AM

Title: A question related to Hofmann elimination
Post by: ino 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.

Title: Re: A question related to Hofmann elimination
Post by: clarkstill 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.

Title: Re: A question related to Hofmann elimination
Post by: ino 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?