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Molecules 2000, 5(2), 127-131;

Unexpected Thorpe Reaction of an α-Alkoxynitrile

Department of Medicinal Chemistry, University of Szeged, Dóm tér 8., H-6720 Szeged, Hungary
Received: 19 January 2000 / Accepted: 14 February 2000 / Published: 17 February 2000
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α-Alkoxynitrile 1 in the presence of tris(methylthio)methyllithium 2 at –78ºC gave the dimer 5 instead of the expected C1-elongated product 3. The formation of compound 5 is explained in terms of anion formation and self-condensation, a variant of the Thorpe reaction. Scrutinizing the 1H NMR spectra revealed that the enamine tautomer 5b is predominant over the imine 5a in the solvents investigated. View Full-Text
Keywords: Thorpe reaction; self-condensation Thorpe reaction; self-condensation

Scheme 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Kovács, L. Unexpected Thorpe Reaction of an α-Alkoxynitrile. Molecules 2000, 5, 127-131.

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