Studies of metal ammonia interactions with aromatic substrates. Final report, December 18, 1979-February 28, 1985

Technical Report · Fri Nov 01 04:00:00 EST 1985

OSTI ID:6436836

Rabideau, P W

This report provides some highlights of the achievements accomplished during the contract period (December 18, 1979 to February 28, 1985) with emphasis on recent work. Major accomplishments lie in two areas, metal-ammonia reduction and reductive alkylation processes, and the conformational analysis of hydroaromatics. This includes the selective reduction of alkyl naphthalenes to 1,2-dihydro, 1,4-dihydro or tetrahydro reduction products, and the application of these techniques to dimeric naphthalenes serving as ''coal models''. We also demonstrated that the presence of water before metal addition has no negative effect on the reduction of polynuclear compounds. Moreover, added water was found to have an unusual, positive effect on the reduction of aromatic esters and allowed 1,4 ring reduction for the first time. We have also learned a great deal about the alkylation of benzylic anions including stereochemical and counterion effects. Finally, our proton and carbon NMR work, as well as empirical force field calculations with 1,4-dihydroaromatics has provided new thinking about the solution stereochemistry of these compounds. Our results suggest planar structures for a number of compounds heretofore considered to be ''boat shaped''. 23 refs., 3 figs.

• Research Organization: Indiana-Purdue Univ., Indianapolis (USA). Dept. of Chemistry
• DOE Contract Number: AC02-79ER10339
• OSTI ID: 6436836
• Report Number(s): DOE/ER/10339-2-Final; ON: DE86004207
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKYLATION
AMMONIA
AROMATICS
CARBONACEOUS MATERIALS
CHEMICAL REACTIONS
COAL
CONDENSED AROMATICS
ENERGY SOURCES
FOSSIL FUELS
FUELS
HYDRIDES
HYDROCARBONS
HYDROGEN COMPOUNDS
ISOMERIZATION
MATERIALS
MOLECULAR STRUCTURE
NAPHTHALENE
NITROGEN COMPOUNDS
NITROGEN HYDRIDES
ORGANIC COMPOUNDS
REDUCTION
STEREOCHEMISTRY