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Related Concept Videos

Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...
π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with an...
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.

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

Published on: November 30, 2022

Transient bis(carboranyl)boryl anions.

Kanika Vashisth1, Ragene A Thornton1, Bohak Yoon1

  • 1Baylor University, Department of Chemistry and Biochemistry One Bear Place #97348 Waco TX 76798 USA caleb_d_martin@baylor.edu.

Chemical Science
|July 13, 2026
PubMed
Summary

Transient boryl anions were generated from bromoboranes with ortho-carborane substituents. Their unique linear singlet ground state, stabilized by carboranes, influences reactivity, enabling new synthetic pathways.

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Area of Science:

  • Organometallic Chemistry
  • Boron Chemistry
  • Computational Chemistry

Background:

  • Carboranes are versatile boron-containing compounds with unique electronic properties.
  • Boryl anions are reactive intermediates crucial for various synthetic transformations.
  • Understanding the electronic structure and reactivity of boryl anions is key to developing new methodologies.

Purpose of the Study:

  • To investigate the generation and electronic structure of boryl anions derived from ortho-carborane substituted bromoboranes.
  • To explore the influence of ortho-carborane substituents on the stability and reactivity of boryl anions.
  • To elucidate novel reaction pathways involving these boryl anions.

Main Methods:

  • Reduction of ortho-carborane substituted bromoboranes.
  • Density Functional Theory (DFT) computations for electronic structure analysis.
  • Investigation of reaction outcomes with different ortho-substituents (phenyl, trimethylsilyl, methyl).

Main Results:

  • Generation of transient boryl anions with an unusual linear singlet ground state.
  • Stabilization of the boryl anion ground state through negative hyperconjugation by ortho-carboranes.
  • Substitution-dependent reactivity: C-H insertion/cyclization with phenyl/trimethylsilyl groups; nucleophilic reactions with methyl groups.

Conclusions:

  • The electronic properties of ortho-carboranes significantly influence the ground state and reactivity of boryl anions.
  • Novel intramolecular reactions (C-H insertion, cyclization) and intermolecular reactions (nucleophilic attack, cycloaddition) were demonstrated.
  • This study expands the synthetic utility of boryl anions in organoboron chemistry.