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Related Concept Videos

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.
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

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Related Experiment Video

Updated: Jun 24, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Amine-triggered molecular capsules using dynamic boronate esterification.

Kenichi Kataoka1, Sachiko Okuyama, Tsuyoshi Minami

  • 1Department of Applied Chemistry, Graduate School of Urban Environmental Sciences, Tokyo Metropolitan University, 1-1 Minami-ohsawa, Hachioji, Tokyo, 192-0397, Japan.

Chemical Communications (Cambridge, England)
|March 19, 2009
PubMed
Summary
This summary is machine-generated.

Researchers developed novel boron-containing molecular capsules activated by amines. These capsules can encapsulate species like cesium ions, showcasing potential for molecular recognition and storage applications.

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Synthesis and Characterization of Functionalized Metal-organic Frameworks
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Synthesis and Characterization of Functionalized Metal-organic Frameworks

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Last Updated: Jun 24, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Synthesis and Characterization of Functionalized Metal-organic Frameworks
11:27

Synthesis and Characterization of Functionalized Metal-organic Frameworks

Published on: September 5, 2014

Area of Science:

  • Supramolecular Chemistry
  • Boron Chemistry

Background:

  • Molecular capsules offer controlled environments for guest molecules.
  • Amine-triggered systems present unique activation mechanisms.

Purpose of the Study:

  • To report the first instance of boron-contained molecular capsules.
  • To investigate amine-triggered capsule formation and guest encapsulation.

Main Methods:

  • Synthesis of novel boron-containing molecular capsules.
  • Solvolysis reactions triggered by triethylamine (Et3N) and n-tributylamine (nBu3N).
  • Characterization of encapsulated species within the molecular cavities.

Main Results:

  • Et3N triggered encapsulation of the Lewis acid Et3NH+ via solvolysis.
  • nBu3N formed a dynamic capsule capable of encapsulating multiple guests, including Cs+.
  • Demonstrated amine-induced control over capsule formation and guest binding.

Conclusions:

  • Boron-contained molecular capsules represent a new class of self-assembled structures.
  • Amine stimuli provide a versatile trigger for capsule formation and guest complexation.
  • These findings open avenues for designing responsive materials for ion capture and storage.