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- W1969811105 endingPage "5674" @default.
- W1969811105 startingPage "5663" @default.
- W1969811105 abstract "Irradiation of 1,2,4,5-tetracyanobenzene (TCNB) with styrene derivatives 1–4, respectively, leads to a photochemical olefin dimerization–aromatic substitution reaction to give the corresponding (2,4,5-tricyanophenyl)tetralin derivative (8, 12, 16, 17, and 20) as the main product. Further irradiation of the primary product with alkene results in substitution of the meta-CN group by another phenyltetralinyl to give the corresponding 4:1 (alkene–TCNB) product. According to the effect of the codonor (biphenyl) and salt (magnesium perchlorate) on reaction rate, the result of photoinduced reactions of TCNB with tetralin (6) and 1-phenyltetralin (7) and analysis of the known kinetic data for relevant processes in the cyanoarene–alkene reactions, the mechanism for the formation of the olefin dimerization–aromatic substitution products (such as 8) is proposed to involve radical pair combination of the alkene cyclodimer radical (the corresponding 4-phenyl-1-tetralinyl radical) with TCNB− followed by expulsion of a CN−. Photoreactions of TCNB with the alkene photocyclodimer (1-phenyltetralin) may also make minor contributions. Photoinduced reaction of TCNB with 1-phenylcyclohexene (5) takes a different pathway from 1–4 to afford the 1:1 (5–TCNB) primary product 21 by deprotonation of 5+ and radical pair combination with TCNB− followed by elimination of HCN." @default.
- W1969811105 created "2016-06-24" @default.
- W1969811105 creator A5011792514 @default.
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- W1969811105 creator A5064835622 @default.
- W1969811105 creator A5073345526 @default.
- W1969811105 creator A5083719043 @default.
- W1969811105 date "2006-06-01" @default.
- W1969811105 modified "2023-09-24" @default.
- W1969811105 title "Photoreactions of 1,2,4,5-benzenetetracarbonitrile with arylethenes—photo- olefin dimerization–aromatic substitution reactions" @default.
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