Carbanion photochemistry. 5. Electron-transfer quenching of carbanion photoreactivity by condensed aromatic hydrocarbons

Journal Article · Fri Jul 02 04:00:00 EDT 1982 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/jo00135a033· OSTI ID:6576090

Tolbert, L M; Merrick, R D

This report examines the ready quenching of triphenylmethyl anion photochemistry by condensed aromatic hydrocarbons and investigates an unusual inverse relationship between acceptor concentration and quantum yield. This photochemistry of triphenylmethyl anion involves formation of 1,1,1-triphenylethane (TPE) as the major product along with diphenyltolylmethane (DTM) through the electron transfer induced decomposition of dimethyl sulfoxide. It was experimentally determined that irradiation of dimethyl sulfoxide solutions of triphenylmethyl anion in the presence of condensed aromatic hydrocarbons leads to efficient quenching of the electron-transfer photochemistry, while addition of tetrahydrofuran induces a change in mechanism from nonchain S/sub RN/1 to S/sub ET/.

• Research Organization: Univ. of Kentucky, Lexington
• OSTI ID: 6576090
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 47:14; 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)
400500* -- Photochemistry
ANIONS
AROMATICS
CHARGED PARTICLES
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CONDENSED AROMATICS
DATA
DMSO
ELECTRON TRANSFER
EXPERIMENTAL DATA
FURANS
HETEROCYCLIC COMPOUNDS
INFORMATION
IONS
IRRADIATION
KINETICS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANIC SOLVENTS
ORGANIC SULFUR COMPOUNDS
QUENCHING
REACTION KINETICS
SOLVENTS
SULFOXIDES
TETRAHYDROFURAN
YIELDS