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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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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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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Reactions at the Benzylic Position: Halogenation01:11

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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Updated: Oct 12, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Tandem Amination/Oxetane Ring Opening toward Benzomorpholines.

Lindsey G DeRatt1, Chao-Yuan Wang1, Scott D Kuduk1

  • 1Janssen Research and Development, 1400 McKean Road, Spring House, Pennsylvania 19477, United States.

The Journal of Organic Chemistry
|November 22, 2021
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Summary

A new tandem method provides efficient access to benzomorpholine scaffolds through C-N coupling and oxetane ring opening. This operationally simple synthesis yields valuable heterocycles in moderate to high yields.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry

Background:

  • The benzomorpholine scaffold is a key structural motif in various biologically active compounds.
  • Efficient synthetic routes to functionalized benzomorpholines are crucial for drug discovery and development.

Purpose of the Study:

  • To develop a rapid and operationally simple tandem approach for synthesizing the benzomorpholine scaffold.
  • To explore the scope and limitations of the developed method regarding substrate functionalization.

Main Methods:

  • A tandem reaction sequence involving C-N coupling (Ullmann or Buchwald-Hartwig conditions) followed by in situ oxetane ring opening.
  • Utilizing a range of aryl substrates with diverse functional groups.

Main Results:

  • Successful synthesis of benzomorpholine derivatives in moderate to high yields.
  • Demonstrated tolerance of various functional groups on the aryl ring.
  • The cyclization product features a pendant hydroxymethyl group, enabling further chemical modifications.

Conclusions:

  • The reported tandem approach offers a streamlined and efficient route to valuable benzomorpholine heterocycles.
  • The method's tolerance for diverse functionalities and the presence of a reactive handle on the product enhance its utility in medicinal chemistry and synthetic endeavors.