Moureau-Mignonac imine synthesis

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The Moureau-Mignonac-Imine-Synthesis is a name reaction in organic chemistry, which is the direct synthesis of imines from nitriles . It was first mentioned by Edmond Blaise in 1901, but was then explored in depth by C. Moureau and G. Mignonac in 1913.

Overview reaction

In this synthesis, the nitrile reacts in methanol with a Grignard compound and an imine is formed.

Moureau-Mignonac imine synthesis overview

Reaction mechanism

The mechanism is explained below:

R 1 and R 2 can be alkyl - or aryl radicals to be

The Grignard compound leads to a nucleophilic addition to the carbon of the nitrile, while the nitrogen forms a bond with the magnesium bromide ( 1 and 2 ). The existing methanol now protonates the amine and the magnesium bromide is split off as alcoholate ( 3 ), creating an imine.

For monosubstituted arylimines , the efficiency of the reaction depends on the position on the remainder, with the following order: meta position> ortho position> para position . In addition, steric hindrances of the residues and the imine-enamine tautomerism can also have an influence on the reaction rate.

See also

Individual evidence

  1. ↑ a b Zerong Wang: Comprehensive Organic Name Reactions and Reagents, 3 Volume Set . John Wiley & Sons, Hoboken, New Jersey 2009, ISBN 978-0-471-70450-8 , pp. 1988-1990.
  2. ↑ JB Culbertson, Donald Butterfield, Ortwin Kolewe, Robert Shaw: Steric Factors in the Hydrolysis Rates of Ketimines. In: The Journal of Organic Chemistry . 27, 1962, pp. 729-733, doi : 10.1021 / jo01050a007 .