1017-93-2Relevant articles and documents
Cycloadditions of Tetracyanoethylene with Dienes and Electron Rich Alkenes: A Search for ET Mechanisms Employing Sensitive Cation Radical Probes
Kim, Taisun,Mirafzal, Gholam A.,Bauld, Nathan L.
, p. 7201 - 7204 (1993)
Cycloadditions of tetracyanoethylene with electron rich alkenes are investigated using sensitive cation radical probes.The results support a direct cycloaddition mechanism as opposed to one involving initial electron transfer.
Reaktivity of Substituted 1,3-Butadienes in Diels-Alder-Reactions
Ruecker, Christa,Lang, Dietrich,Sauer, Juergen,Friege, Henning,Sustmann, Reiner
, p. 1663 - 1690 (2007/10/02)
Kinetic data for the reaction of substituted 1,3-dienes with tetracyanoethylene (TCNE) and other dienophiles are interpreted in terms of the FMO-model.While the expectations are fulfilled qualitatively, the kinetic data cannot be correlated quantitatively.This shows that in Diels-Alder reactions besides HOMO-LUMO separation other factors play an important role, for instance the 1,4-distance in the diene and the conformational equilibrium cisoid transoid of the diene.The kinetic data are in accord with a one-step mechanism of the cycloaddition reaction.