Metal-ammonia ring reduction of aromatic carboxylic acid esters
Journal Article
·
· J. Org. Chem.; (United States)
Although esters are often reduced to alcohols with metal-ammonia solutions, it has been found that aromatic carboxylic acid esters can be reduced efficiently to the corresponding dihydro aromatics when 1.25 equiv of water is present before metal addition. The general effect of the presence of water (before metal addition) upon metal-ammonia reduction of polycyclics was tested with anthracene (0.5 g), which was reduced to 9,10-dihydroanthracene (97% yield) in the presence of 3.5 g of water. Polynuclear aromatic esters are reduced smoothly by this technique, but in the absence of water, alkyl 9-anthroates gave a dimer assigned as axial/axial on the basis of nuclear Overhauser enhancements. Possible mechanistic pathways for dimer formation were investigated by the addition of 9,10-dihydroanthracene monoanion as well as anthracene dianion to ammonia/THF solutions of ethyl anthroate. This led to dimer and trimer formation, respectively. The structures of these compounds are discussed in light of their carbon and proton NMR spectra.
- Research Organization:
- Indiana Univ.-Purdue Univ., Indianapolis
- OSTI ID:
- 6823292
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 49:9; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALCOHOLS
AMMONIA
AROMATICS
CARBOXYLIC ACID ESTERS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
DATA
ELEMENTS
ESTERS
EXPERIMENTAL DATA
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INFORMATION
METALS
MOLECULAR STRUCTURE
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NMR SPECTRA
NUMERICAL DATA
ORGANIC COMPOUNDS
OXYGEN COMPOUNDS
POLYCYCLIC AROMATIC HYDROCARBONS
REDUCTION
SPECTRA
WATER
YIELDS
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALCOHOLS
AMMONIA
AROMATICS
CARBOXYLIC ACID ESTERS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
DATA
ELEMENTS
ESTERS
EXPERIMENTAL DATA
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INFORMATION
METALS
MOLECULAR STRUCTURE
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
NMR SPECTRA
NUMERICAL DATA
ORGANIC COMPOUNDS
OXYGEN COMPOUNDS
POLYCYCLIC AROMATIC HYDROCARBONS
REDUCTION
SPECTRA
WATER
YIELDS