May 07, 2021, 09:12:10 PM
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Topic: Problem witch Birch reduction  (Read 185 times)

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Offline w.uzar

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Problem witch Birch reduction
« on: March 07, 2021, 05:25:57 PM »
The reaction of anisole gives a 1-methoxycyclohexa-1,4-diene as a product of the birch reduction.

Could someone help me with the following issues and outline the reaction mechanisms?

1) Why does a 1-methoxycyclohexa-1,4-diene reaction with an acid that does not contain a nucleophilic anion give a 1-methoxycyclohexa-1,3-diene? What is the mechanism?

2) Why does a 1-methoxycyclohexa-1,4-diene reaction with an diluted acid give a cyclohex-3-en-1-one? What is the mechanism?

3) Why does a 1-methoxycyclohexa-1,4-diene reaction with an concentrated acid give a cyclohex-2-en-1-one? What is the mechanism?

Thank you very much for your answer!

Offline rolnor

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Re: Problem witch Birch reduction
« Reply #1 on: March 08, 2021, 08:32:25 AM »
I give you a hint: Vinyl ether

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