Unexpected Thorpe Reaction of an α-Alkoxynitrile
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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2000-02-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/5/2/127/ |
| Summary: | 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. |
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| ISSN: | 1420-3049 |