Journal of the American Chemical Society p. 4561 - 4563 (1989)
Update date:2022-08-11
Topics:
Czekay, Gregor
Drewello, Thomas
Schwarz, Helmut
The study of D-labeled 5-cyanononane isotopomers in the gas phase provides evidence that the Fe+-mediated remote functionalization of nitriles, resulting in the regiospecific generation of H2 and C2H4 from the ω and (ω - 1) position of the alkyl chain, can be described as follows: (i) Oxidative addition of a methyl C-H bond is not rate limiting.For the generation of C2H(4-x)Dx it is the elimination of the olefin which is associated with kinetic isotope effects comparable to the ones reported earlier for other systems. (ii) The generation of H(2-x)Dx is affected bytwo isotope effects.One concerns the β-hydrogen transfer (kH/kD = 1.59) and the other the reductive elimination of hydrogen (kH2/kHD = 1.70 and kHD/kD2 = 1.44).
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