Carbanion photochemistry. 3. Electron transfer and radical-anion control in the photochemistry of triphenylmethyl anion

Journal Article · Wed Oct 22 04:00:00 EDT 1980 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00542a023· OSTI ID:6903970

Tolbert, L M

On the basis of concentration and competition studies, the photomethylation of triphenylmethyl anion in dimethyl sulfoxide is shown to involve the reaction of methyl radical with triphenylmethyl anion to yield the radical anions of 1,1,1-triphenylethane and 3-(diphenylmethylene)-6-methyl-1,4-cyclohexadiene. However, there are no chain-carrying steps as there are for typical S/sub RN/1 reactions. The intervention of radical anions produces the unconventional product of para alkylation, but the reaction is dominated by the bond strength of the newly formed bond as indexed by pK/sub a/.

• Research Organization: Univ. of Kentucky, Lexington
• OSTI ID: 6903970
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 102:22; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400500* -- Photochemistry
ALKYL RADICALS
ANIONS
AROMATICS
CHARGED PARTICLES
CHEMICAL REACTION KINETICS
CHEMISTRY
DMSO
ELECTRON TRANSFER
IONS
KINETICS
METHYL RADICALS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PHOTOCHEMISTRY
RADICALS
REACTION KINETICS
SULFOXIDES