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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Accessing Medium-Sized Rings via Vinyl Carbocation Intermediates.

Zhenqi Zhao1, Stasik Popov2, Woojin Lee2

  • 1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Organic Letters
|January 31, 2024
PubMed
Summary
This summary is machine-generated.

Synthesizing medium-sized rings (8-11 members) is difficult. This study introduces a catalytic method using vinyl carbocation intermediates for efficient 8- and 9-membered ring formation via Friedel-Crafts reactions.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Medium-sized rings (8-11 membered) present synthetic challenges due to ring strain compared to smaller rings (5-7 membered).
  • Efficient construction of medium-sized carbocycles remains a key objective in organic synthesis.

Purpose of the Study:

  • To develop a novel catalytic method for the synthesis of 8- and 9-membered rings.
  • To overcome the synthetic difficulties associated with medium-sized ring formation.

Main Methods:

  • Employing intramolecular Friedel-Crafts reactions.
  • Generating vinyl carbocation intermediates catalytically.
  • Utilizing a Lewis acidic lithium cation-weakly coordinating anion salt for ionization of vinyl toluenesulfonates.

Main Results:

  • Successful catalytic formation of 8- and 9-membered rings.
  • Demonstration of a novel route to medium-sized carbocycles.
  • The method proceeds via vinyl carbocation intermediates.

Conclusions:

  • A new catalytic approach enables efficient synthesis of medium-sized rings.
  • The developed method overcomes common challenges in medium-sized ring construction.
  • This work provides a valuable tool for accessing 8- and 9-membered carbocycles.