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- W2952297384 abstract "Irradiation of 4-chloroaniline or of its N,N-dimethyl derivative in polar solvents generates the corresponding triplet phenyl cations. These are trapped by alkenes yielding arylated products in medium to good yields. B3LYP calculations show that the triplet cation slides with negligible activation energy to a bonded adduct with ethylene, whereas it forms only a marginally stabilized CT complex with water (chosen as a representative σ nucleophile). The structure of the final products depends on the preferred path from the adduct cation with the alkene. In the case of aryl olefins, this deprotonates to stilbene derivatives, while, from 2,3-dimethyl-2-butene and allytrimethylsilane, allylanilines are obtained by elimination of an electrofugal group in γ. In the case of mono- and disubstituted alkenes the cation adds chloride rather than eliminating and β-chloroalkylanilines are obtained. The regio- and sterochemistry of the addition across the alkene are best understood with a phenonium ion structure for the..." @default.
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- W2952297384 date "2010-05-22" @default.
- W2952297384 modified "2023-09-25" @default.
- W2952297384 title "ChemInform Abstract: Photoinduced, Ionic Meerwein Arylation of Olefins." @default.
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- W2952297384 doi "https://doi.org/10.1002/chin.200205087" @default.
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