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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.
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
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.
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).

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Related Experiment Video

Updated: Jun 4, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

New polycyclic borazine species.

Xiaochen Xie1, Mairi F Haddow, Stephen M Mansell

  • 1School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK.

Chemical Communications (Cambridge, England)
|February 26, 2011
PubMed
Summary
This summary is machine-generated.

New polycyclic borazines were synthesized from diborate(4) anions and characterized. Their structures and bonding were analyzed and compared to polycyclic aromatic hydrocarbons.

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Area of Science:

  • Inorganic Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Borazines are inorganic heterocyclic compounds with unique electronic properties.
  • Polycyclic aromatic hydrocarbons (PAHs) are a well-studied class of organic molecules with diverse applications.
  • Exploring novel polycyclic structures can lead to new materials with tailored characteristics.

Purpose of the Study:

  • To synthesize and structurally characterize novel polycyclic borazine compounds.
  • To investigate the bonding and structural features of these new borazines.
  • To compare the properties of these borazines with those of analogous polycyclic aromatic hydrocarbons.

Main Methods:

  • Synthesis of polycyclic borazines from diborate(4) anions and B(2)Cl(2)(NMe(2))(2).
  • Structural characterization using X-ray diffraction and other spectroscopic techniques.
  • Computational analysis of electronic structure and bonding.

Main Results:

  • Successful synthesis of three new polycyclic borazines: B(2){1,2-N(2)C(6)H(4)}(2){B(2)(NMe(2))(2)}(2), B(2){1,8-N(2)naph}(2){B(2)(NMe(2))(2)}(2), and B(2)(NPh)(4){B(2)(NMe(2))(2)}(2).
  • Detailed structural data revealing unique polycyclic frameworks.
  • Analysis of B-N and B-C bonding within the novel structures.

Conclusions:

  • The new polycyclic borazines exhibit distinct structural and electronic properties.
  • Comparison with PAHs provides insights into structure-property relationships.
  • These findings expand the scope of known borazine architectures and their potential applications.