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...
| Main Author: | |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2000-02-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/5/2/127/ |
| _version_ | 1819088906476322816 |
|---|---|
| author | Lajos Kovács |
| author_facet | Lajos Kovács |
| author_sort | Lajos Kovács |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-21T21:59:29Z |
| format | Article |
| id | doaj.art-b3e0470f03094796b1be1b38c9606ff2 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T21:59:29Z |
| publishDate | 2000-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b3e0470f03094796b1be1b38c9606ff22022-12-21T18:48:51ZengMDPI AGMolecules1420-30492000-02-015212713110.3390/50200127Unexpected Thorpe Reaction of an α-AlkoxynitrileLajos Kovácsα-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.http://www.mdpi.com/1420-3049/5/2/127/Thorpe reactionself-condensation |
| spellingShingle | Lajos Kovács Unexpected Thorpe Reaction of an α-Alkoxynitrile Molecules Thorpe reaction self-condensation |
| title | Unexpected Thorpe Reaction of an α-Alkoxynitrile |
| title_full | Unexpected Thorpe Reaction of an α-Alkoxynitrile |
| title_fullStr | Unexpected Thorpe Reaction of an α-Alkoxynitrile |
| title_full_unstemmed | Unexpected Thorpe Reaction of an α-Alkoxynitrile |
| title_short | Unexpected Thorpe Reaction of an α-Alkoxynitrile |
| title_sort | unexpected thorpe reaction of an aza alkoxynitrile |
| topic | Thorpe reaction self-condensation |
| url | http://www.mdpi.com/1420-3049/5/2/127/ |
| work_keys_str_mv | AT lajoskovaƒacs unexpectedthorpereactionofanazaalkoxynitrile |