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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.
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.
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.
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,...
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

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Updated: Jul 3, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
09:22

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Boron-based rotaxanes by multicomponent self-assembly.

Nicolas Christinat1, Rosario Scopelliti, Kay Severin

  • 1Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, Switzerland.

Chemical Communications (Cambridge, England)
|July 31, 2008
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel rotaxanes using a multicomponent reaction involving pyridyl-ethylene, catechol, boronic acid, and crown ethers. X-ray crystallography confirmed the formation of these complex molecular architectures.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Crystallography

Background:

  • Rotaxanes are mechanically interlocked molecules with potential applications in nanotechnology.
  • Developing efficient synthetic routes to complex rotaxanes remains a key challenge in supramolecular chemistry.

Purpose of the Study:

  • To synthesize novel rotaxane structures via a multicomponent reaction.
  • To characterize the synthesized rotaxanes using X-ray crystallography.

Main Methods:

  • A multicomponent reaction involving 1,2-di(4-pyridyl)ethylene, catechol, and 3,5-bis(trifluoromethyl)phenylboronic acid.
  • Incorporation of macrocyclic components: 1,5-dinaphtho-38-crown-10 or bis-para-phenylene-34-crown-10.
  • Structural elucidation using X-ray crystallography.

Main Results:

  • Successful synthesis of rotaxanes through a one-pot multicomponent reaction.
  • X-ray crystallography confirmed the threaded structure of the rotaxanes.
  • The reaction demonstrated versatility with two different crown ether variants.

Conclusions:

  • The multicomponent reaction provides an efficient pathway for rotaxane synthesis.
  • The characterized rotaxanes represent new building blocks for advanced molecular machines.
  • X-ray crystallography is crucial for verifying the complex architectures of rotaxanes.