The dissolving metal reduction of polynuclear aromatic compounds

Conference · Mon Sep 01 04:00:00 EDT 1986 · Am. Chem. Soc., Div. Pet. Chem., Gen. Pap., Prepr.; (United States)

OSTI ID:7043119

Rabideau, P W

The reaction of benzene and its derivatives with alkali metals in liquid ammonia with alcohol cosolvent, is known as the ''Birch Reduction''. As expected with anionic intermediates, 1-substituted-1, 4-dihydro products result from electron withdrawing groups, and 2, 5-dihydro products with electron donors. Application of these conditions to polynuclear aromatic compounds (PA's) (1c) resulted in complications, since the initially formed products were themselves subject to reduction under the reaction conditions. Although methods such as the use of iron salts were devised to minimize such complications, more recently developed procedures avoid the use of alcohol altogether, and employ stronger quenching agents like water or ammonium chloride added after reaction with the alkali metal is complete. In the absence of alcohols, it was also found that the PA/alkali metal solutions could be reacted with alkyl halides to produce dialkylated products (e.g., anthracene) (1c).

• Research Organization: Purdue School of Science at Indianapolis, Indiana Univ., Purdue Univ. at Indianapolis, Indianapolis, IN
• OSTI ID: 7043119
• Report Number(s): CONF-860911-
• Conference Information: Journal Name: Am. Chem. Soc., Div. Pet. Chem., Gen. Pap., Prepr.; (United States) Journal Volume: 31:3
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALCOHOLS
ALKALI METALS
ALKYL RADICALS
ALKYLATION
AMMONIA
AMMONIUM CHLORIDES
AMMONIUM COMPOUNDS
AMMONIUM HALIDES
ANTHRACENE
AROMATICS
BENZENE
CHARGED-PARTICLE REACTIONS
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
CONDENSED AROMATICS
DISSOLUTION
ELECTRON REACTIONS
ELEMENTS
HALIDES
HALOGEN COMPOUNDS
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
ION PAIRS
IRON CHLORIDES
IRON COMPOUNDS
KINETICS
LEPTON REACTIONS
METALS
NAPHTHALENE
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NUCLEAR REACTIONS
ORGANIC COMPOUNDS
OXYGEN COMPOUNDS
POLYCYCLIC AROMATIC HYDROCARBONS
QUENCHING
RADICALS
REACTION INTERMEDIATES
REACTION KINETICS
REDUCTION
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS
WATER