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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Regioselectivity of Electrophilic Additions-Peroxide Effect

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.
Halogenation of Alkenes02:46

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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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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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...

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Nanomechanics of Drug-target Interactions and Antibacterial Resistance Detection
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Bromado selectivo del sitio de la vancomicina.

Tejas P Pathak1, Scott J Miller

  • 1Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, USA.

Journal of the American Chemical Society
|April 3, 2012
PubMed
Resumen

Los investigadores lograron la brominación selectiva del sitio de la vancomicina, creando nuevas monobromovancomicinas. Un promotor de péptido mejoró las tasas de reacción y alteró la distribución del producto para la modificación de la vancomicina.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • Química Medicinal Química medicinal es el campo de la química medicinal.
  • La bioquímica es la bioquímica.

Sus antecedentes:

  • La vancomicina es un antibiótico crítico para el tratamiento de infecciones bacterianas graves Gram-positivas.
  • La modificación de la vancomicina puede superar los mecanismos de resistencia emergentes.
  • La funcionalización selectiva del sitio de moléculas complejas como la vancomicina sigue siendo un desafío.

Objetivo del estudio:

  • Desarrollar un método para la brominación selectiva del sitio de la vancomicina.
  • Para investigar la influencia de los promotores en la brominación de la vancomicina.
  • Explorar condiciones alternativas para el control de la funcionalización de la vancomicina.

Principales métodos:

  • Bromado directo de la vancomicina mediante el uso de N-bromoftalimida.
  • Utilizando un promotor basado en péptidos diseñado racionalmente para influir en la reactividad.
  • Investigando el efecto del disolvente y la guanidina como sustitutos del promotor del péptido.

Principales resultados:

  • Eficiencia sustancial en la producción de nuevas monobromovancomicinas, una dibromovancomicina y una tribromovancomicina.
  • Se ha demostrado una aceleración significativa de la velocidad de brominación de la vancomicina con el promotor del péptido.
  • Se observó una distribución alterada del producto y una selectividad de sitio alternativa influenciada por el promotor, el disolvente y la guanidina.

Conclusiones:

  • La brominación selectiva del sitio de la vancomicina se puede lograr con alta eficiencia.
  • Los promotores basados en péptidos pueden mejorar significativamente y controlar la funcionalización de la vancomicina.
  • Los disolventes y aditivos alternativos como la guanidina ofrecen una mayor capacidad de ajuste para la modificación de la vancomicina.