| Autor: |
Peša, Nela, Welch, Chris J., Boa, Andrew N. |
| Zdroj: |
Journal of Heterocyclic Chemistry; May 2005, Vol. 42 Issue: 4 p599-607, 9p |
| Abstrakt: |
A simple reaction affording E1dimethylamino2phenylsulfonylethylene, and SE2N,NdimethylaminoethenylSphenylNptolylsulfonyl sulfoximide in high yields is described. A reversal in regioselectivity was observed when the βdimethylaminovinyl sulfone was employed as a dipolarophile in cycloadditions with nitrile oxides. The sulfone gives rise mainly to 4substituted isoxazoles, after elimination of dimethyl amine. In comparison, phenyl vinyl sulfone cycloadds to give 5substituted isoxazolines. Although not showing comparable dipolarophilic activity in reactions with nitrile oxides and nitrile imides, the βdimethylaminovinyl sulfoximide was easily converted to SE3ethoxycarbonylprop2enylSphenylNptolylsulfonyl sulfoximide. This allylic sulfoximide cycloadds in good yield to both benzonitrile oxide and diphenylnitrile imide, but no stereoselectivity was observed in the process; and only modest regioselectivity was detected in the case of benzonitrile oxide. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
|
Plný text