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Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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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.
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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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.
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Carbocations02:10

Carbocations

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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...
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.8K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.8K
Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

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Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Developing nitrosocarborane chemistry.

Samuel L Powley1, Louise Schaefer, Wing Y Man

  • 1Institute of Chemical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK. a.j.welch@hw.ac.uk.

Dalton Transactions (Cambridge, England : 2003)
|January 27, 2016
PubMed
Summary
This summary is machine-generated.

New bright-blue nitrosocarboranes were synthesized and characterized. Water was found to reduce nitrosocarboranes to hydroxylamine species during aqueous work-up, a process that can be avoided with non-aqueous methods.

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Area of Science:

  • Organometallic Chemistry
  • Boron Chemistry
  • Synthetic Chemistry

Background:

  • Carboranes are a class of organoboron compounds with unique cage structures.
  • Nitrosocarboranes are derivatives with potential applications in various chemical transformations.
  • Understanding the reactivity and stability of nitrosocarboranes is crucial for their synthetic utility.

Purpose of the Study:

  • To synthesize and characterize novel nitrosocarborane compounds.
  • To investigate the influence of the nitroso group on carborane properties.
  • To explore the reactivity of nitrosocarboranes, particularly in Diels-Alder reactions.

Main Methods:

  • Synthesis of nitrosocarboranes via lithiocarborane reaction with nitronium chloride (NOCl).
  • Characterization using spectroscopic (NMR) and crystallographic techniques.
  • Investigation of reaction mechanisms, including isotopic labeling studies to probe water's role.

Main Results:

  • Successful synthesis of several new nitrosocarborane derivatives, characterized as bright-blue compounds.
  • The nitroso group bonds as a 1e substituent with minimal impact on 11B NMR chemical shifts.
  • Demonstrated the utility of nitrosocarboranes in Diels-Alder cycloaddition reactions, leading to novel derivatives.

Conclusions:

  • Nitrosocarboranes are stable under non-aqueous conditions but can be reduced to hydroxylamines in the presence of water.
  • The nitroso group's electronic influence on the carborane cage is minimal.
  • Nitrosocarboranes serve as valuable synthons for constructing complex carborane architectures via cycloaddition reactions.