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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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Radical Reactivity: Nucleophilic Radicals01:16

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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
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Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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Alkali Metals03:06

Alkali Metals

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Group 1 elements are soft and shiny metallic solids. They are malleable, ductile, and good conductors of heat and electricity. The melting points of the alkali metals are unusually low for metals and decrease going down the group, while the density increases going down the group with the exception of potassium (Table 1).
Table 1: Properties of the alkali metals
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
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Cómo los alcóxidos de metales alcalinos inician reacciones de radicales orgánicos

Seb Tyerman1, Kenneth F Clark1, Alexander J Stewart1

  • 1Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, U.K.

Journal of the American Chemical Society
|February 20, 2026
PubMed
Resumen

Los alcóxidos de metales alcalinos inician la química radicalaria a través de intermedios de bencino, no por transferencia de electrones. Este estudio revela la formación simultánea de múltiples tipos de bencinos y un novedoso mecanismo de metilación.

Palabras clave:
alcóxidos de metales alcalinoshaluros de ariloquímica radicalariaintermedios de bencinotransferencia de electronesmetilación

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Área de la Ciencia:

  • Química Orgánica; Mecanismos de Reacción

Sus antecedentes:

  • Se sabe que los alcóxidos de metales alcalinos facilitan la hidrodeshalogenación y las reacciones de acoplamiento de haluros de arilo.; Se pensaba previamente que estas reacciones involucraban intermedios de radicales arilo formados a través de la transferencia de electrones desde los alcóxidos.

Objetivo del estudio:

  • Investigar el mecanismo por el cual los alcóxidos de metales alcalinos reaccionan con haluros de arilo.; Determinar si la transferencia de electrones o la desprotonación inician la química radicalaria.

Principales métodos:

  • Se emplearon estudios de isótopos de deuterio para investigar el mecanismo de reacción.; Se realizaron reacciones con varios alcóxidos de metales alcalinos, incluido el terc-butóxido de potasio.

Principales resultados:

  • El estudio refuta el mecanismo de transferencia de electrones, mostrando que la desprotonación conduce a intermedios de bencino que inician la química radicalaria.; Se observó la formación simultánea de bencinos orto-, meta-, para- y remotos.; Se identificó un novedoso mecanismo de metilación de arenes a través de radicales metilo derivados del terc-butóxido.

Conclusiones:

  • El mecanismo establecido que involucra la transferencia de electrones para formar radicales arilo es incorrecto.; Los intermedios de bencino son clave para la química radicalaria iniciada por los alcóxidos de metales alcalinos.; Los hallazgos revelan nuevas perspectivas sobre la formación de bencinos y la química radicalaria derivada de alcóxidos.