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MeO MeO OH The nucleophilic phenolate oxygen atom of adds to the carbon of the thioester group; then ethylthiolate is eliminated. One of these possibilities is represented next.
The phenolate ion in the Chapter 3 Reactions of Nudeophiles and Bases right-hand ring of reduces the acidity of the other phenoUc group in that ring. Thus, we anticipate that the proton of the second phenoUc group is removed in a later step.
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MeO OH Both mechanisms for the reaction seem reasonable. The authors of the paper cited Abell et al. Note that is the phenol corresponding to the intermedi- ate phenolate of mechanism 2.
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This evidence does not prove that is an intermediate in the reaction, but does support it as a viable possibility. How would you change the mechanism to make it more reasonable? Base-Promoted Rearrangements 4 I Write step-by-step mechanisms for the following transformations. Lithium diisopropylamide LDA is a strong base, but not a good nucleo- phile because of steric inhibition by the two isopropyl groups directly at- tached to the nitrogen anion.
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I , This means that a symmetrical intermediate must be formed. The Benzilic Acid Rearrangement This is a rearrangement of an a-diketone, in base, to give an a-hydroxy- carboxylic acid. Base-Promoted Rearrangements The final steps, under the reaction conditions, are protonation of the alkoxide and deprotonation of the carboxyUc acid to give the corresponding carboxyl- ate sah.
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A History of the Nomenclature of Organic Chemistry
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