Organic Chemistry Portal



Ammonia Free Partial Reduction of Aromatic Compounds Using Lithium Di-tert-butylbiphenyl (LiDBB)

Timothy J. Donohoe* and David House

*Dyson Perrins Laboratory, South Parks Road, Oxford OX1 3QY, U.K., Email:

T. J. Donohoe, D. House, J. Org. Chem., 2002, 67, 5015-5018.

DOI: 10.1021/jo0257593

see article for more examples


The reduction of various hetero- and carbocyclic aromatic compounds under ammonia free conditions uses LiDBB as a source of electrons, bis(methoxyethyl)amine (BMEA) as a protonating agent, and THF as a solvent. In contrast to Birch type conditions, the described ammonia free conditions allow the use of reactive electrophiles.

see article for more examples

Key Words

Birch reduction, 1,4-cyclohexadienes (by reduction), 3-pyrrolines, 2,5-dihydrofurans, Lithium

ID: J42-Y2002-1770