July 22, 2024, 03:49:39 PM
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Topic: ethyl chloroformate for claisen addition-----double addition?  (Read 764 times)

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Offline Allendo

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Hi Team,
For Claisen addition, the classic product is a 1,3 dicarbonyl. If I use ethyl chloroformate as the electrophile and the nucleophile is a symmetric ketone (meaning only a possible enolate), the product is a simply addition with ethyl chloroformate kicking off the -Cl group. When I google online or read the textbook, it seems people stops here.

But my question is: it appears to me that the ester part of the ethyl chloroformate is again a decent leaving group for Claisen reaction. Therefore, I would predict the final product should be a meso 1,3,5 tricarbonyl. (because of the plane of symmetry). Am I right? Or is it controlled by the concentration of both of the reactants?


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