Abstract
Regioselectivity patterns for the reactions of
N
-lithio-
N
-vinylaniline with several arenedicarboxylates and esters of α,β-unsaturated acids are reported.
N
-Lithio-
N
-vinylaniline reacted at both of its ambident anionic sites, to give β-enamino ketones and amide derivatives. A bridgehead compound resulting from cycloadditions involving
N
-lithio-
N
-vinylaniline was also formed in the reactions with ethyl cinnamate and ethyl phenylpropiolate. The structures of all compounds formed were fully characterised by NMR techniques.