Generation of arenium ions by a self-protonation reaction in an aprotic molten salt medium

Journal Article · Wed Jul 30 04:00:00 EDT 1980 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00536a024· OSTI ID:5069301

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

We have examined the reaction behavior of a group of polycyclic aromatic hydrocarbons in the aprotic liquid SbC1/sub 3/-10 mol % AlCl/sub 3/ from 100 to 130/sup 0/C by /sup 1/H NMR and by quench and separation techniques. For anthracene, pyrene, 9,10-dimethylanthracene, 9,10-diphenylanthracene, and naphthacene, we have observed a novel arene self-protonation reaction for which the proton source is the condensation-dehydrogenation of a portion of the arene combined with arene oxidation by SbCl/sub 3/. Naphthalene and phenanthrene, however, do not undergo this reaction. Evidence is presented which indicates that the self-protonation reaction proceeds through the oxidation of the arene to its radical cation by SbCl/sub 3/, and that the function of AlCl/sub 3/ is to enhance the oxidizing power of the Sb/sup 3 +//Sb/sup 0/ couple.

• Research Organization: Oak Ridge National Lab., TN
• DOE Contract Number: W-7405-ENG-26
• OSTI ID: 5069301
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 102:16; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALUMINIUM CHLORIDES
ALUMINIUM COMPOUNDS
ANTHRACENE
ANTIMONY CHLORIDES
ANTIMONY COMPOUNDS
AROMATICS
CHEMICAL REACTIONS
CHEMICAL SHIFT
CHLORIDES
CHLORINE COMPOUNDS
CONDENSED AROMATICS
DEHYDROGENATION
HALIDES
HALOGEN COMPOUNDS
HIGH TEMPERATURE
HYDROCARBONS
MAGNETIC RESONANCE
MEDIUM TEMPERATURE
MOLTEN SALTS
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
OXIDATION
POLYCYCLIC AROMATIC HYDROCARBONS
PYRENE
QUENCHING
RESONANCE
SALTS