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• W4252888777 abstract "The photochemical reactivity of a series of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenylethene in a nucleophilic solvent (methanol) has been investigated. Analysis of the photochemical reactions involving the 4-halobenzonitriles revealed formation of alkene-methanol adducts, such as 1-methoxy-2,2-diphenylethane, 1-methoxy-2,2-diphenylethene, and 1,1-dimethoxy-2,2-diphenylethane, indicative of a photochemical electron-transfer mechanism. These products were not significant in the photochemical reactions involving the 4-haloanisoles. Both the 4-halobenzonitriles and the 4-haloanisoles produced an arene-alkene-methanol Markovnikov adduct, 1-aryl-2-methoxy-2,2-diphenylethane (aryl = 4-cyanophenyl or 4-methoxyphenyl). This compound was shown to undergo an acid-catalysed elimination to 1-aryl-2,2-diphenylethene under the reaction conditions, which subsequently underwent a 6pi-electrocyclization to the 3-substituted(cyano or methoxy)-9-phenylphenanthrene. Possible mechanisms for the observed reactivity are discussed and evaluated.Key words: photochemistry, photoinduced electron transfer, bond homolysis, radical ions, radicals, exciplexes." @default.
• W4252888777 created "2022-05-12" @default.
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• W4252888777 date "1999-10-01" @default.
• W4252888777 modified "2023-10-03" @default.
• W4252888777 title "The photochemistry of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenylethene in methanol. Homolytic cleavage versus electrontransfer pathways" @default.
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• W4252888777 doi "https://doi.org/10.1139/v99-185" @default.
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