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Related Concept Videos

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
Phase I Reactions: Hydrolytic Reactions01:15

Phase I Reactions: Hydrolytic Reactions

Hydrolysis, a cornerstone of phase I biotransformation reactions, uses water to cleave chemical bonds. This process is pivotal in drug metabolism, generating more polar metabolites that can be easily excreted.
An important hydrolytic reaction is ester hydrolysis. Ester bonds, often found in prodrugs, are broken down, increasing the solubility of drugs like aspirin and lidocaine for more straightforward elimination. Amide hydrolysis is another critical reaction, targeting amide bonds prevalent...

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Continuous hydroamination in a liquid-liquid two-phase system.

Volker Neff1, Thomas E Müller, Johannes A Lercher

  • 1Lehrstuhl für Technische Chemie II, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany.

Chemical Communications (Cambridge, England)
|July 19, 2002
PubMed
Summary
This summary is machine-generated.

This study demonstrates efficient hydroamination catalysis using a two-phase system. This method allows for continuous catalytic hydroamination reactions with various substrates.

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Area of Science:

  • Catalysis
  • Organic Chemistry
  • Green Chemistry

Background:

  • Hydroamination, the addition of an N-H bond across a carbon-carbon multiple bond, is a key transformation in organic synthesis.
  • Developing efficient and sustainable catalytic systems for hydroamination remains an important goal in chemical research.

Purpose of the Study:

  • To develop and demonstrate an efficient catalytic system for direct hydroamination reactions.
  • To investigate the use of a liquid-liquid two-phase system for continuous hydroamination processes.

Main Methods:

  • Utilized a polar catalyst phase consisting of Zn(CF3SO3)2 in the ionic liquid 1-ethyl-3-methylimidazolium trifluoromethanesulfonate.
  • Employed a liquid-liquid two-phase system with the catalyst in the ionic liquid phase and the substrate mixture in heptane.
  • Demonstrated the continuous catalysis of various hydroamination reactions.

Main Results:

  • Achieved efficient catalysis of direct hydroamination reactions.
  • Successfully implemented a liquid-liquid two-phase system for continuous hydroamination.
  • Showcased the versatility of the catalytic system for different hydroamination reactions.

Conclusions:

  • The developed two-phase system provides an efficient and potentially scalable method for hydroamination.
  • This approach offers advantages for continuous processing in organic synthesis.
  • The catalytic system demonstrates broad applicability for various hydroamination reactions.