Video Experimental Relacionado

Updated: Jul 20, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Adición de metanol a los complejos de renio dihapto-coordinados de furanos

L A Friedman¹, W D Harman

¹Department of Chemistry, University of Virginia, Charlottesville, VA 22901, USA.

Journal of the American Chemical Society

|September 13, 2001

Resumen

Los complejos de renio-furano se someten a adición de metanol catalizado por ácido, dando lugar a una síntesis estereoselectiva de complejos de metoxidihidrofurano. La adición del grupo methoxy es consistentemente anti para el fragmento de metal, con relaciones de producto independientes de las relaciones de material de partida.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
Química sintética de la química sintética.

Sus antecedentes:

Se conocen complejos de renio con ligandos de furano.
Se han sintetizado mezclas diastereoméricas de estos complejos.

Objetivo del estudio:

Para investigar la adición de metanol catalizado por ácido a los complejos [TpRe (((CO) (((L)) ((4,5-eta ((2) -furan) ].
Para caracterizar los complejos resultantes dihapto-coordinados de 2-metoxi-2,3-dihidrofurano y los productos de éter vinílico.

Principales métodos:

Reacción de los complejos [TpRe(CO) ((L) ((4,5-eta(2)-furan) ] con el metanol bajo condiciones ácidas a -40°C.
Análisis de la formación de productos diastereoméricos y la estereoselectividad.

Principales resultados:

Síntesis de dos diastereómeros de complejos de 2-metoxi-2,3-dihidrofurano para L = (t) BuNC, PMe(3), piridina y 1-metilimidazol.
Anti-adición estereoselectiva del grupo metoxico en relación con el fragmento de metal.
Formación de un producto de éter vinílico a partir del complejo (t) BuNC a través de la abertura del anillo de furano.

Conclusiones:

La adición de metanol catalizado por ácido a estos complejos de renio-furano proporciona una ruta a los dihidrofuranos funcionalizados.
El resultado estereoquímico se rige por la anti-adición del grupo metoxí.
Las proporciones diastereoméricas del producto no se correlacionan con las proporciones del material de partida.

Más Videos Relacionados

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphos^Ph Complexes

Published on: April 10, 2015

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Videos de Conceptos Relacionados

Hydroboration-Oxidation of Alkenes

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.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Radical Anti-Markovnikov Addition to Alkenes: Overview

Radical Anti-Markovnikov Addition to Alkenes: Overview

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

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

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 radical...