Development of degradative techniques for coal chemistry based on ether cleavage reactions and metal arene chemistry
The degradation of C-O and C-C bonds have been examined using model compounds that are similar in structure to those found in coal and other natural products. The conditions to maximize ether cleavage and minimize the formation of undesirable side products were determined by varying the concentration of reagents, temperature, and reaction time. 2-Phenoxynaphthalene (1) and 1-methoxypyrene (2) were the compounds examined. The optimum conditions demonstrated complete disappearance of 1 and 2, mass recoveries were above 84%, and the formation of reduced dimers in less than 10 mole % yield. The possibility of cleaving a C-C bond by a (3+2) cycloaddition and subsequent cycloreversion reactions was examined by treating a variety of dipolarphiles with deprotonated (({eta}{sup 6}-arene)FeCp){sup +} complexes (arene = hexamethylbenzene or tetralin) Azides and ozone were found to add quantitatively to the metal-arene complexes. Upon decomplexation of the ring, moderated yields of benzyl substituted products were isolated. The mechanism of this reaction is yet unknown but is postulated to occur by direct nucleophilic addition of the complex anion to the most electropositive atom of the dipolarphile. Chemical and electrochemical oxidation techniques were applied to the deprotonated (({eta}{sup 6}-arene)FeCp){sup +} complexes. Only minor yields of benzylic oxidation products were observed.
- Research Organization:
- North Dakota Univ., Grand Forks, ND (USA)
- OSTI ID:
- 5002849
- Resource Relation:
- Other Information: Thesis (Ph. D.)
- Country of Publication:
- United States
- Language:
- English
Similar Records
An investigation of the photochemical properties of transition metal arene complexes: Final report for the period July 1, 1983 to June 30, 1987
Metal arene complexes in coal structure determination: Quarterly report for the period June 1987-August 1987
Related Subjects
CHEMICAL BONDS
CLEAVAGE
COAL
STRUCTURAL CHEMICAL ANALYSIS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
COMPLEXES
CONDENSED AROMATICS
CYCLOALKANES
ELECTROCHEMISTRY
ETHERS
OPTIMIZATION
OXIDATION
REDUCTION
SODIUM
TEMPERATURE DEPENDENCE
TIME DEPENDENCE
ALKALI METALS
ALKANES
AROMATICS
CARBONACEOUS MATERIALS
CHEMISTRY
CRYSTAL STRUCTURE
ELEMENTS
ENERGY SOURCES
FOSSIL FUELS
FUELS
HYDROCARBONS
KINETICS
MATERIALS
METALS
MICROSTRUCTURE
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
REACTION KINETICS
010600* - Coal
Lignite
& Peat- Properties & Composition