Unexpected Thorpe Reaction of an α-Alkoxynitrile

doi:10.3390/50200127

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Molecules 2000, 5(2), 127-131; doi:10.3390/50200127

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Unexpected Thorpe Reaction of an α-Alkoxynitrile

Lajos Kovács

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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Abstract: 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.

Keywords: Thorpe reaction; self-condensation

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MDPI and ACS Style

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

AMA Style

Kovács L. Unexpected Thorpe Reaction of an α-Alkoxynitrile. Molecules. 2000; 5(2):127-131.

Chicago/Turabian Style

Kovács, Lajos. 2000. "Unexpected Thorpe Reaction of an α-Alkoxynitrile." Molecules 5, no. 2: 127-131.

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