Dicationic electrophiles from olefinic amines in superacid
| HERO ID | 5417775 |
|---|---|
| In Press | No |
| Year | 2003 |
| Title | Dicationic electrophiles from olefinic amines in superacid |
| Authoring Organization | U.S. Department of Defense |
| Journal | Journal of Organic Chemistry |
| Volume | 68 |
| Issue | 13 |
| Page Numbers | 5119-5122 |
| Abstract | This paper describes the superacid-catalyzed chemistry of olefinic amines and related compounds. A variety of olefinic amines are found to react with benzene in CF(3)SO(3)H (triflic acid) to give addition products in good yields (75-99%), including the pharmaceutical agents fenpiprane and prozapine. A general mechanism is proposed that invokes the formation of reactive, dicationic electrophiles and the direct observation of a diprotonated species is reported from low-temperature NMR experiments. This chemistry is also used to conveniently prepare functionalized polystyrene beads having pendant amine groups. |
| Doi | 10.1021/jo030024z |
| Pmid | 12816465 |
| Wosid | WOS:000183669800013 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Scopus URL: https://www.scopus.com/inward/record.uri?eid=2-s2.0-0037872105&doi=10.1021%2fjo030024z&partnerID=40&md5=a5c37b1c773cc34b8c605efffc1e6210 |
| Is Public | Yes |
| Language Text | English |