Molten salt catalyzed transfer hydrogenation of polycyclic aromatic hydrocarbons. selective hydrogenation of anthracene and naphthacene by tetralin in molten antimony trichloride

Journal Article · Fri Jan 01 04:00:00 EST 1982 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00343a001· OSTI ID:5593610

Buchanan, III, A C; Dworkin, A S; Smith, G P

Anthracene and naphthacene are selectively hydrogenated by tetralin to 9,10-dihydroanthracene and 5,12-dihydronaphthacene, respectively, in a reaction that is catalyzed by molten SbCl/sub 3/ at 80/sup 0/C. In situ /sup 1/H NMR studies indicate that under similar conditions, phenanthrene and pyrene do not react, while perylene is partially oxidized to a persistent radical cation. For the tetralin transfer hydrogenation of anthracene and naphthacene, product analysis shows that no naphthalene is formed, but that the dehydrogenated tetralin reacts with itself and unreacted arene to give alkylated products. These transfer hydrogenation reactions can best be explained by a redox initiated ionic mechanism involving the arene radical cation and the 1-tetralyl cation (1,2,3,4-tetrahydro-1-naphthalenylium ion) as key intermediates.

• Research Organization: Oak Ridge National Lab., TN
• DOE Contract Number: W-7405-ENG-26
• OSTI ID: 5593610
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 47:4; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ANTHRACENE
ANTIMONY CHLORIDES
ANTIMONY COMPOUNDS
AROMATICS
CATALYTIC EFFECTS
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
CONDENSED AROMATICS
HALIDES
HALOGEN COMPOUNDS
HYDROCARBONS
HYDROGEN TRANSFER
HYDROGENATION
MOLTEN SALTS
ORGANIC COMPOUNDS
POLYCYCLIC AROMATIC HYDROCARBONS
REDOX REACTIONS
SALTS
TETRALIN