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

Unexpected Thorpe Reaction of an α-Alkoxynitrile

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 Thorpe reaction; self-condensation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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