July 18, 2024, 01:57:07 AM
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Topic: Mannich reaction on Furfuryl alcohol  (Read 712 times)

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Offline AUSTRIANGUY

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Mannich reaction on Furfuryl alcohol
« on: June 19, 2024, 06:43:33 PM »
I am having trouble figuring out the mechanism for the Mannich reaction on Furfuryl alcohol. I understand first step (the formation of the iminium ion), but i do not understand how this would react with Furfuryl alcohol. In Literature i only find how it would take place with a carbonylgroup. Any suggestions? Thanks in advance.

Offline rolnor

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Re: Mannich reaction on Furfuryl alcohol
« Reply #1 on: June 22, 2024, 06:49:30 AM »
It sound confusing. You need a carbonyl, is it furfural you mean? Or maybe there is another molecule that you missed out?

Offline spirochete

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Re: Mannich reaction on Furfuryl alcohol
« Reply #2 on: July 07, 2024, 02:09:14 PM »
https://www.sciencedirect.com/science/article/abs/pii/S0040403900860645

It is something like this probably ^^^. The furan is a nucleophile. If we focus on the furan component then this would be electrophilic aromatic substitution. Furans are activated nucleophiles for EAS that react at the two position.

It seems furfuryl alcohol really enjoys polymerizing in acid, so that could be problematic for sure if you attempt some other process like Mannich with it.

It could also be something like Rolnor describes, where the initial description of the alcohol is a typo.

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