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Topic: Eschweiler-Clarke Reaction  (Read 4169 times)

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Offline beheada

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Eschweiler-Clarke Reaction
« on: October 22, 2007, 10:00:19 AM »
I'm trying to understand the mechanism behind this reaction. The mechanism can be found at <A HREF="http://www.organic-chemistry.org/namedreactions/eschweiler-clarke-reaction.shtm">HERE</A>. My question involves the protonation to the imine followed by the addition of the formic acid anion and loss of CO2. What causes the initial protonation in this case? It would seem that the molecule is stable as an amino-alcohol? What leads to the reduction?

Offline AWK

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Re: Eschweiler-Clarke Reaction
« Reply #1 on: October 22, 2007, 10:25:09 AM »
Formic acid is a weak one, but still acid. Eventually you may use a small amount of a stronger acid as catalyst
AWK

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