Model compound study of the mechanism of sp/sup 2/-sp/sup 3/ carbon-carbon cleavage during the reduction of coals. [Bibenzyl, diphenylmethane,. cap alpha. -benzylnaphthalene]

Conference · Wed Dec 31 23:00:00 EST 1980

OSTI ID:6065293

Collins, C J; Hombach, H P; Maxwell, B E; Benjamin, B M

The sp/sup 3/-sp/sup 2/ bonds in bibenzyl can cleave in the presence of Na(K) at 0/sup 0/ in glyme and triglyme by simple fragmentation of the substrate radical anion. In the case of diphenylmethane itself, the sp/sup 2/-sp/sup 3/ bond is too strong to be cleaved by simple fragmentation. In this event cleavage occurs through a bimolecular reaction between a diphenylmethane molecule and a diphenylmethane radical anion. When the reaction of diphenylmethane with NaK is carried out in the presence of benzene, a bimolecular reaction between benzene radical anion and diphenylmethane occurs yielding, among other products, toluene, biphenyl, and hydrogenated biphenyls. ..cap alpha..-Benzylnaphthalene, under the same reaction conditions, appears to cleave both by fragmentation of the benzylnaphthalene radical anion, eq. (9), as well as by ipso-nucleophilic attack of the radical anion on ..cap alpha..-benzylnaphthalene.

• Research Organization: Oak Ridge National Lab., TN (USA)
• DOE Contract Number: W-7405-ENG-26
• OSTI ID: 6065293
• Report Number(s): CONF-810914-4; ON: DE81029685
• Country of Publication: United States
• Language: English

Related Subjects

01 COAL, LIGNITE, AND PEAT
010600 -- Coal
Lignite
& Peat-- Properties & Composition
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKALI METALS
AROMATICS
BIBENZYL
CARBONACEOUS MATERIALS
CHEMICAL BONDS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
COAL
CONDENSED AROMATICS
ELEMENTS
ENERGY SOURCES
ETHERS
FOSSIL FUELS
FRAGMENTATION
FUELS
HYDROCARBONS
KINETICS
LOW TEMPERATURE
MATERIALS
METALS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
POTASSIUM
REACTION KINETICS
REDUCTION
SODIUM
TOLUENE