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Issue 1, 1994
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Variable regioselectivity in reactions of N-lithio-N-vinylaniline with arenedicarboxylates and α,β-unsaturated esters

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.

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Article type: Paper
DOI: 10.1039/P19940000113
Citation: J. Chem. Soc., Perkin Trans. 1, 1994, 113-118
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    Variable regioselectivity in reactions of N-lithio-N-vinylaniline with arenedicarboxylates and α,β-unsaturated esters

    A. R. Katritzky, D. C. Oniciu, B. Mancheño and R. A. Barcock, J. Chem. Soc., Perkin Trans. 1, 1994, 113
    DOI: 10.1039/P19940000113

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