Module 3 : Organometallic Reagents

Lecture 20 : Organomagnesium Reagents

    

Synthesis of Primary Amines


The reaction of chloramines with organomagnesium halides gives primary amines (Scheme 15).

Scheme 15


Synthesis of Deutrated Hydrocarbons


Deutrated hydrocarbons can be synthesized by the reaction of organomagnesium halides with D2O (Scheme 16).

Scheme 16


There are several reactions employing organomagnesium halides that have their own names

Benary Reaction

It provides an effective method for the synthesis of α,β -unsaturated carbonyl compounds from β -( N,N -dialkylamino)-vinyl ketone and Grignard reagent by 1,4-addition followed by hydrolysis and elimination of the dialkylated amine.

Bodrous Reaction

This reaction provides a method for the preparation of substituted amides from aliphatic or aromatic esters and an aminomaganesium halide which can be obtained from a primary or secondary amine and Grignard reagent at room temperature.

Bouveault Reaction

Primary alkyl halide can be converted into aldehydes with an additional carbon via the formation of Grignard reagent followed by reaction with N,N -disubstituted formamide and hydrolysis.

Dzhemilev Reaction

It involves the reaction of alkenes with Grignard reagent to give alkyl magnesium halide in the presence of Cp2ZrCl2 . This method had found wide application in organic and organometallic synthesis.

Kulinkovich Reaction

The reaction of esters with dialkyldialkoxytitanium reagents, generated in situ from Grignard reagents bearing hydrogen in β -position and titanium(IV) alkoxides such as titanium isopropoxide , gives cyclopropanols.