Polar Substituent Effects in Additions of Alkyl Radicals to Alkenes
Reduction of cyclohexylmercuric salts (7) with NaBH4 yields cyclohexyl radicals (8).Their rel. rates of addition to substituted styrenes 4, acrylic esters 5 and acrylonitriles 6 have been measured.Comparison with Hammett ?-values shows, that substituents at the non attacked vinylic carbon atom show polar effects mainly (Table 1).The effect of a substituent variation increases with increase of the reactivity of the alkenes (Table 2).Mesomeric and steric effects play only a minor role.
Giese, Bernd,Meixner, Juergen
p. 2138 - 2145
(2007/10/02)
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