Mloston, G; Kania, K; Heimgartner, H (2009). Chemoselective insertion of dimethoxycarbene into the N-H bond of thiolactams with diverse ring size. Journal of Sulfur Chemistry, 30(3-4):278-286.
Thermal decomposition of 2,5-dihydro-1,3,4-oxadiazole 4 in toluene solution in the presence of thiolactams 7 or corresponding lactams 11 result in the chemoselective formation of the N-(dimethoxy)methyl derivatives 8 and 12, respectively. The products of both types are formed via insertion of dimethoxycarbene 2a into the N−H bonds. A reaction mechanism via the intermediate ion pair 14/15 or a complex of type 13 is postulated to explain the formation of the products.
Thermal decomposition of 2,5-dihydro-1,3,4-oxadiazole 4 in toluene solution in the presence of thiolactams 7 or corresponding lactams 11 result in the chemoselective formation of the N-(dimethoxy)methyl derivatives 8 and 12, respectively. The products of both types are formed via insertion of dimethoxycarbene 2a into the N−H bonds. A reaction mechanism via the intermediate ion pair 14/15 or a complex of type 13 is postulated to explain the formation of the products.
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Scopus Subject Areas: | Physical Sciences > General Chemistry |
| Language: | English |
| Date: | June 2009 |
| Deposited On: | 25 Nov 2009 12:57 |
| Last Modified: | 23 Jan 2022 14:59 |
| Publisher: | Taylor & Francis |
| ISSN: | 1741-5993 |
| Funders: | Rector of the University of Lodz |
| OA Status: | Closed |
| Publisher DOI: | https://doi.org/10.1080/17415990902870935 |
Mloston, G