Formation of unexpected products in the attempted aziridination of styrene with trifluoromethanesulfonyl nitrene
- The reaction of styrene with trifluoromethanesulfonyl nitrene generated from trifluoromethanesulfonamide in the system (t-BuOCl+NaI) results in the formation of trifluoro-N-[2-phenyl-2-(trifluoromethylsulfonyl) aminoethyl]methanesulfonamide, 1-pheny1-2-iodo-ethanol, and 2,5-diphenyl-1,4-bis(trifluoromethyl sulfonyl)piperazine rather than the expected product of aziridination, 2-phenyl-1-(trifluoromethylsulfonyl) aziridine. The mechanism of the reaction is discussed.
| Author details: | Bagrat A. Shainyan, Mikail Yu Moskalik, Ines StarkeORCiD, Uwe SchildeORCiDGND |
|---|---|
| URL: | http://www.sciencedirect.com/science/journal/00404020 |
| DOI: | https://doi.org/10.1016/j.tet.2010.08.070 |
| ISSN: | 0040-4020 |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2010 |
| Publication year: | 2010 |
| Release date: | 2017/03/24 |
| Source: | Tetrahedron. - ISSN 0040-4020. - 66 (2010), 43, S. 8383 - 8386 |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
