Photolysis of vinyl halides. Preferential formation of vinyl cations by copper(II) salts

Journal Article · Wed May 14 00:00:00 EDT 1986 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00270a023· OSTI ID:5454768

Kitamura, T; Kobayashi, S; Taniguchi, H

Photolysis of vinyl halides in the presence of copper(II) salts resulted in a significant suppression of product formation derived from vinyl radicals. Photolysis of 1,1-diaryl-2-bromopropenes in the presence of copper(II) salts yielded no 1,1-diaryl-2-propenes. Photolysis of other vinyl halides, i.e., 1,1-diaryl-2-iodopropenes, 1,1-diaryl-2-bromoethylenes, and 1-bromo-2-(p-methoxyphenyl)ethylene, also led to a large decrease in the yields of the reduced olefins derived from the vinyl radicals. Copper(II) triflate was found to be more effective for the oxidation of vinyl radicals than copper(II) acetate. These reactions are explained by the intervention of vinylcopper intermediates and the formation of vinyl cations.

• Research Organization: Kyushu Univ., Fukuoka, Japan
• OSTI ID: 5454768
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 108:10; 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
ALKYL RADICALS
AROMATICS
CATIONS
CHARGED PARTICLES
CHEMICAL REACTIONS
COPPER
DATA
DECOMPOSITION
ELEMENTS
EXPERIMENTAL DATA
HALOGENATED AROMATIC HYDROCARBONS
INFORMATION
IONS
METALS
MONOMERS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXIDATION
PHOTOCHEMICAL REACTIONS
PHOTOLYSIS
RADICALS
REACTION INTERMEDIATES
SALTS
TRANSITION ELEMENTS
VINYL MONOMERS
VINYL RADICALS