Mloston, Grzegorz; Romanski, Jaroslaw; Heimgartner, Heinz (2001). Reactions of Thioesters with Organic Azides - A Novel Access to Imidates and Thioimidates. Polish Journal of Chemistry, 75(7):975-982.
The reaction of O-methyl thiocarboxylates 8a, b with organic azides at 110°C yielded the corresponding imidates of type 9, which were easily hydrolyzed to give amides 10. The formation of 9 can be rationalized by a 1,3-dipolar cycloaddition of the azide with the C=S group, followed by the 'two-fold extrusion' of N2 and S. The analogous reaction with methyl dithiobenzoate (11) led to thioimidates 13. On heating, the latter were transformed into thioamides 12.
The reaction of O-methyl thiocarboxylates 8a, b with organic azides at 110°C yielded the corresponding imidates of type 9, which were easily hydrolyzed to give amides 10. The formation of 9 can be rationalized by a 1,3-dipolar cycloaddition of the azide with the C=S group, followed by the 'two-fold extrusion' of N2 and S. The analogous reaction with methyl dithiobenzoate (11) led to thioimidates 13. On heating, the latter were transformed into thioamides 12.
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Language: | English |
| Date: | 2001 |
| Deposited On: | 23 Oct 2013 06:45 |
| Last Modified: | 24 Sep 2019 19:41 |
| Publisher: | Polskie Towarzystwo Chemiczne |
| ISSN: | 0137-5083 |
| Funders: | Polish State Committee for Scientific Research (Grant No. 3 TO9A 007 16), Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel |
| OA Status: | Closed |
| Related URLs: | http://www.ichf.edu.pl/pjch/pj-2001/pj072001.htm |
| Project Information: |
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Mloston, Grzegorz