Journal of Organic Chemistry p. 5143 - 5147 (1981)
Update date:2022-08-04
Topics:
Kwart, H.
George, T. J.
Horgan, A. G.
Lin, Y. T.
The temperature dependence of kH/kD for the formation of benzaldehyde through base-catalyzed HNO2 elimination from benzyl nitrate is indicative of a tunneling pathway of linear proton transfer.The same criterion applied to the uncatalyzed, gas-phase reaction reveals a cyclic transition state of nonlinear proton transfer.From these and other considerations it has been deduced that the base-catalyzed reaction is best formulated as a cyclic process of linear H transfer and is consistent with an ECO1cb rather than the ECO2 mechanism previously claimed.
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