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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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...
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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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Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance
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Oxime decorated cavitands functionalized through solvent-assisted grinding.

Christer B Aakeröy1, Prashant D Chopade

  • 1Department of Chemistry, Kansas State University, Manhattan, Kansas 66503, United States. aakeroy@ksu.edu

Organic Letters
|December 3, 2010
PubMed
Summary

Researchers developed a new method to create supramolecular capsules using functionalized cavitands. This solvent-assisted grinding technique efficiently converts aldehydes to oximes, yielding high-quality capsules for hydrogen bonding applications.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Supramolecular capsules require functionalized host structures for assembly.
  • Cavitands are versatile scaffolds for creating complex molecular architectures.
  • Hydrogen bonding is a key interaction for self-assembling molecular systems.

Purpose of the Study:

  • To report the synthesis of novel cavitand-based host structures.
  • To functionalize cavitands with aldoxime groups for capsule formation.
  • To develop an efficient method for the final oxime formation step.

Main Methods:

  • Synthesis of four distinct cavitands with varying depths and volumes.
  • Functionalization of cavitands with four aldoxime groups each.
  • Utilizing 'solvent assisted grinding' for the aldehyde to oxime transformation.

Main Results:

  • Successfully synthesized four unique cavitand derivatives.
  • Achieved high yields in the aldehyde to oxime conversion.
  • Demonstrated the capability of these cavitands to form capsules via hydrogen bonding.

Conclusions:

  • Developed a reliable synthetic route for functionalized cavitands.
  • Solvent-assisted grinding is an effective method for oxime formation in this system.
  • The synthesized cavitands are suitable building blocks for supramolecular capsule construction.