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Topic: Wohl Degradation Reagent Inquiry  (Read 1843 times)

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Offline beardy

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Wohl Degradation Reagent Inquiry
« on: November 27, 2015, 06:59:34 PM »
In Wohl degradation, one carbon is removed from a carbohydrate chain.
The following sequential reagents are mentioned:

1) NH2OH
2) acetic anhydride
3) NaOMe

Would acid chloride be an appropriate substitute for step 2? My reasoning is that acid chlorides are more reactive than acetic anhydrides and should therefore work.

Offline phth

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Re: Wohl Degradation Reagent Inquiry
« Reply #1 on: November 30, 2015, 05:27:03 AM »
Acid chlorides are more reactive, but acetic anhydride is easier to handle.  The time of the reaction will vary.

Offline Dan

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Re: Wohl Degradation Reagent Inquiry
« Reply #2 on: November 30, 2015, 07:14:26 AM »
The presence of acetate may speed up the nitrile formation step, depending on what the RDS is. If you use an acid chloride, the acetylation will be faster, but the elimination of acetic acid the will be slower.
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Offline beardy

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Re: Wohl Degradation Reagent Inquiry
« Reply #3 on: December 01, 2015, 02:04:18 AM »
Thanks  ;D

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