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Author Topic: Question about the Wolff-Kishner reduction  (Read 1878 times)

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johnnydepp2012

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Question about the Wolff-Kishner reduction
« on: February 07, 2012, 08:22:33 PM »

Hello,

First off, I'd like to introduce myself, as this is my first post here. I am a senior at a state university getting my degree in chemistry.

I have to do a presentation on a name reaction that was selected for me by my professor at the end of the semester, and I was given the Wolff-Kishner reduction with the Huang-Minglon modification.

I feel like there isn't as much information about this reaction as there is about the other reactions that were given to other students (for example, the Birch reduction).

I have to give a history of the reaction, the scope and limitations of the reaction, and how it is used in organic synthesis today.

I had a few questions that I would really appreciate if someone gave me some help with.

First, will the Wolff-Kishner reduction react with any other functional groups to produce undesirable side products?

Will it break certain ring structures? For example, would it crack open a methylenedioxy ring?

Are there certain ketones (or aldehydes) that will not participate in the reaction? For example, when preparing oxindole from isatin, why aren't both ketones reduced? Does it have to be a beta ketone?

Lastly, why and when would the Huang-Minglon modification be preferred over the two-step Wolff-Kishner reduction? Does the one=pot reaction lead to higher yields?

Thanks for the help, I really appreciate it.

JD
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Dan

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Re: Question about the Wolff-Kishner reduction
« Reply #1 on: February 07, 2012, 10:06:54 PM »

Look for review articles - there are two such articles from the '40s referenced on the wikipedia entry for the W-K reduction.

Also here is a review article and a reference to a another review is provided within. So that's 4 reviews already - see if you have the full text for them in your library.

The conditions for W-K reduction are heat around 200 oC in the presence of KOH (strong base) and hydrazine (excellent nucleophile). Can you think of any functional groups that will react under those conditions other than aldehydes and ketones?
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Arctic-Nation

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Re: Question about the Wolff-Kishner reduction
« Reply #2 on: February 08, 2012, 08:18:36 AM »

Are there certain ketones (or aldehydes) that will not participate in the reaction? For example, when preparing oxindole from isatin, why aren't both ketones reduced? Does it have to be a beta ketone?
That's because the second carbonyl is not a ketone, bobby.
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