Ethylenediamine NH3 alternative for Birch

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THE MOST CLANDESTINE SUITABLE SUBSTITUTE FOR LIQUID AMMONIA IS ETHYLENEDIAMINE


Ethylenediamine (en) is a solvent that can be used in a variation of the Birch reduction, a chemical reaction that reduces aromatic rings to 1,4-cyclohexadienes. This variant, sometimes referred to as Birch-type reduction, uses lithium metal and ethylenediamine in THF (tetrahydrofuran) as an alternative to the traditional liquid ammonia Birch reduction.

Elaboration:
Birch Reduction:
The traditional Birch reduction employs liquid ammonia and an alkali metal (like lithium or sodium) to reduce aromatic compounds to 1,4-cyclohexadienes.

Ethylenediamine as an Alternative Solvent:
Ethylenediamine, when used in combination with lithium metal and THF, provides an alternative solvent system for Birch-type reductions.


Advantages of the Ethylenediamine Variant:
This variant offers several advantages, including:
Simpler Handling: Ethylenediamine and THF are generally less hazardous and easier to handle than liquid ammonia, reducing the need for specialized equipment and cryogenic temperatures.

Scalable: The reaction has been scaled up to gram scale, making it more practical for research and development.

Simpler Workup: The reaction workup is simplified, often involving quenching with water, evaporation of THF, and partitioning.


*You can also substitute lithium for sodium metal *

? Would potassium metal dissolve blue electrons ?


The attachment pictures are excerpts from Uncle Fester

Thank you
 

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