July 22, 2019, 06:03:30 AM
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Topic: Grignard from Acid Chloride  (Read 179 times)

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Offline CKabes

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Grignard from Acid Chloride
« on: May 10, 2019, 10:48:06 AM »
Suppose I take an acid chloride and add magnesium in the same way I would prepare a Grignard reagent from an alkyl chloride. Does the magnesium add into the C-X bond? Is this reagent nucleophilic? I can't find any discussion about this elsewhere.

O=C(C)Cl>[Mg]>O=C([Mg]Cl)C

Offline rolnor

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Re: Grignard from Acid Chloride
« Reply #1 on: May 10, 2019, 12:37:12 PM »
It does not work to make Grignard this way but you can make 1,2-diketones by reacting an acid chloride with pyrophoric lead. If you use umpolung-chemistry you can have a masked nucleophilic carbonylgroup;

https://en.m.wikipedia.org/wiki/Umpolung#Carbonyl_umpolung
« Last Edit: May 10, 2019, 03:10:21 PM by rolnor »

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