Tetrahedron p. 875 - 887 (1985)
Update date:2022-07-25
Topics:
Boucher, Jean-Luc
Stella, Lucien
The Diels-Alder reactivity of two captodative olefins, 2-morpho-lino-acrylonitrile 15 and 2-(N-methlanilino) -acrylonitrile 16, towards four conjugated dienes is evaluated.In every cases, isomeric {4+2} cyclo-adducts are obtained.With olefin 15 yields are better than with olefin 16. The adducts are easily transformed in to the corresponding ketones by a mild hydrolysis of the α-aminonitrile group. Thus, the 1-cyanoenamines can be considered as good ketene equivalents very useful for the synthesis of unsaturated cyclohexanones.
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