Question
Download Solution PDFThe major product formed in the following transformation is
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CSIR-UGC (NET) Chemical Science: Held on (26 Nov 2020)
Answer (Detailed Solution Below)
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Download Solution PDFConcept:
- The Nazarov cyclization reaction is a chemical reaction used in organic chemistry for the synthesis of various cyclopentenone derivatives.
- The Nazarov cyclization involves the activation of a divinyl ketone using a stoichiometric amount of lewis acid or protic acid as a promoter. The key step of the reaction mechanism involves a cationic 4π-electrocyclic ring closure which forms the cyclopentenone product.
- An example is shown below:
Explanation:
- The reaction pathway is shown below:
- From the above reaction, we see that the reaction proceeds through the Nazarov cyclization reaction, where FeCl3 acts as a lewis acid in this reaction to form a cationic intermediate.
- In the next step, the cationic intermediate undergoes a 4π-electrocyclic ring closure in a conrotatory manner to give the \(\beta \)-silyl carbocation.
- The silyl carbocation undergoes rearrangement to give the final product.
Conclusion:
The major product formed in the following transformation is
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