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The lithium derivative of propargyl chloride reacts with diethyl oxalate to give ethyl 5-chloro-2-oxopent-3-ynoate. Under mild conditions, this ester undergoes Diels-Alder reactions with conjugated dienes of various structure. The adducts formed from five-membered cyclic dienes exist as stable enols and the adducts from cyclohexadiene and 2,3-dimethylbuta-1,3-diene exist in the keto form.
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