2007
DOI: 10.5012/bkcs.2007.28.7.1217
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Kinetics and Mechanism of the Addition of Benzylamines to α-Thiophenyl-β-phenylacrylonitriles in Acetonitrile

Abstract: Addition of amines (XRNH 2 ) to olefins (YC 6 H 4 CH= CZZ') is known to proceed in acetonitrile by concerted formation of the C β -N and C α -H bonds in a single-step process leading to a neutral product, 1 I. This is, however, quite in contrast to the mechanism in aqueous solution, which occurs through a zwitterionic intermediate, II (T ± ), with imbalanced transition states (TSs) in which the development of resonance into the activating (electronacceptor) group (Z,Z') lags behind charge transfer of bond … Show more

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